No renderable structure data available
C1=CC(=CC(=C1)N)CS(=O)(=O)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | (3-aminophenyl)methanesulfonamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 344750-15-8 |
| Database ID | 13266255 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
(3-aminophenyl)methanesulfonamide (CAS 344750-15-8) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 13266255
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-759c9b76d7474470b71e809bc3986d79Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: G2 was prepared from (3-aminophenyl)methanesulfonamide (85 mg, 0.46 mmol) and A1 (100 mg, 0.46 mmol) following the procedure reported for G1 by heating in DMF for 3 hours, and it was obtained as a colorless amorphous solid (3.1 mg, 2%). 1H NMR (400 MHz, d6-DMSO, 300K) δ 3.79 (s, 3H), 4.15 (s, 2H), 6.73 (bs, 2H), 6.84 (dd, J=5.3 Hz, J=1.5 Hz, 1H), 6.96-6.98 (m, 1H), 7.04 (dt, J=1.0 Hz, J=8.0 Hz, 1H), 7.13 (d, J=8.2 Hz, 1H), 7.21-7.25 (m, 2H), 7.33 (dd, J=7.6 Hz, J=1.8 Hz, 1H), 7.36-7.42 (m, 1H), 7.64-7.68 (m, 2H), 8.14 (d, J=5.3 Hz, 1H), 9.08 (s, 1H). MS (ES) C19H19N3O3S requires: 369. found: 370 (M+H)+.
Source ID: ord-d1ad620c41384b74a22676e341579bc4Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Intermediate A2 (119 mg, 0.5 mmol), (3-aminophenyl)methanesulfonamide (112 mg, 0.6 mmol), NaOC(CH3)3 (67 mg, 0.7 mmol), PdCl2(CH3CN)2 (6.5 mg, 0.025 mmol, 5 mol %), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) [Xantphos] (23 mg, 0.04 mmol, 8 mol %) were dissolved in dry DMF (4 mL) and purged for 10 minutes with nitrogen. After heating at 110° C. for 18 hours the reaction mixture was filtered and the residue washed with toluene. The filtrate was concentrated under reduced pressure and purified by automated column chromatography (ISCO, gradient MeOH/DCM). The collected fractions which contained the title compound were further purified by preparative HPLC to yield 24 mg (12%) of G1 as an off-white solid. 1H NMR (300 MHz, d6-DMSO, 298K) δ 3.84 (s, 3H), 4.22 (s, 2H), 6.81-6.94 (m, 5H), 6.98 (s, 1H), 7.07 (dd, J=11.7 Hz, J=4.2 Hz, 1H), 7.26 (t, J=6.6 Hz, 1H), 7.39 (dd, J=6.9 Hz, J=6.0 Hz, 1H), 7.56-7.61 (m, 1H), 7.79 (d, J=7.5 Hz, 1H), 8.16 (d, J=6.0 Hz, 1H), 9.12 (s, 1H). purged for 10 minutes with nitrogen was filtered the residue washed with toluene The filtrate was concentrated under reduced pressure purified by automated column chromatography (ISCO, gradient MeOH/DCM) were further purified by preparative HPLC to yield 24 mg (12%) of G1 as an off-white solid
Source ID: ord-c67929852bdb4a339566a7461158a5ddConditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Intermediate A2 (119 mg, 0.5 mmol), (3-aminophenyl)methanesulfonamide (112 mg, 0.6 mmol), NaOC(CH3)3 (67 mg, 0.7 mmol), PdCl2(CH3CN)2 (6.5 mg, 0.025 mmol, 5 mol %), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) [Xantphos] (23 mg, 0.04 mmol, 8 mol %) were dissolved in dry DMF (4 mL) and purged for 10 minutes with nitrogen. After heating at 110° C. for 18 hours the reaction mixture was filtered and the residue washed with toluene. The filtrate was concentrated under reduced pressure and purified by automated column chromatography (ISCO, gradient MeOH/DCM). The collected fractions which contained the title compound were further purified by preparative HPLC to yield 24 mg (12%) of G1 as an off-white solid. 1H NMR (300 MHz, d6-DMSO, 298K) δ 3.84 (s, 3H), 4.22 (s, 2H), 6.81-6.94 (m, 5H), 6.98 (s, 1H), 7.07 (dd, J=11.7 Hz, J=4.2 Hz, 1H), 7.26 (t, J=6.6 Hz, 1H), 7.39 (dd, J=6.9 Hz, J=6.0 Hz, 1H), 7.56-7.61 (m, 1H), 7.79 (d, J=7.5 Hz, 1H), 8.16 (d, J=6.0 Hz, 1H), 9.12 (s, 1H). purged for 10 minutes with nitrogen was filtered the residue washed with toluene The filtrate was concentrated under reduced pressure purified by automated column chromatography (ISCO, gradient MeOH/DCM) were further purified by preparative HPLC to yield 24 mg (12%) of G1 as an off-white solid
Source ID: ord-c67929852bdb4a339566a7461158a5ddConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,4-dichloro-1,3,5-triazine (1.0 eq) in dry DMF (0.7 M) at 0° C. under N2 atmosphere was added a solution of (3-aminophenyl)-methanesulfonamide (1.0 eq) in dry DMF (0.7 M). The reaction mixture was stirred for 2.5 h at 0° C. Then water was added and the aqueous solution was neutralized with sat. aq. NaHCO3 solution. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4. Evaporation of solvent gave A1 as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, d6-DMSO, 300K) δ 4.26 (s, 2H), 6.89 (s, 2H), 7.15 (d, J=7.4 Hz, 1H), 7.36 (d, J=7.4 Hz, 1H), 7.66 (d, J=7.4 Hz, 1H), 8.64 (s, 1H), 9.75 (br. s, 1H), 10.83 (s, 1H). MS (ES) C10H10ClN5O2S requires: 299. found: 300 (M+H)+. The aqueous layer was extracted with EtOAc the combined organic layers were dried over Na2SO4 Evaporation of solvent
Source ID: ord-4c537d3662694d899423edc50d09fd9bConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,4-dichloro-1,3,5-triazine (1.0 eq) in dry DMF (0.7 M) at 0° C. under N2 atmosphere was added a solution of (3-aminophenyl)-methanesulfonamide (1.0 eq) in dry DMF (0.7 M). The reaction mixture was stirred for 2.5 h at 0° C. Then water was added and the aqueous solution was neutralized with sat. aq. NaHCO3 solution. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4. Evaporation of solvent gave A1 as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, d6-DMSO, 300K) δ 4.26 (s, 2H), 6.89 (s, 2H), 7.15 (d, J=7.4 Hz, 1H), 7.36 (d, J=7.4 Hz, 1H), 7.66 (d, J=7.4 Hz, 1H), 8.64 (s, 1H), 9.75 (br. s, 1H), 10.83 (s, 1H). MS (ES) C10H10ClN5O2S requires: 299. found: 300 (M+H)+. The aqueous layer was extracted with EtOAc the combined organic layers were dried over Na2SO4 Evaporation of solvent
Source ID: ord-4c537d3662694d899423edc50d09fd9bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-759c9b76d7474470b71e809bc3986d79Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 2-chloro-4-(2-methoxy-phenyl)-pyrimidine (0.882 g, 0.004 mol), and (3-amino-phenyl)-methanesulfonamide (0.865 g, 0.005 mol) in DMF (12 ml) was stirred for 2 hours at 80° C. (TLC control). The solvent was removed under reduced pressure to afford {3-[4-(2-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-methanesulfonamide. The solvent was removed under reduced pressure
Source ID: ord-b0626daba0fe42d19f59e25de4583afbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (3-Nitrophenyl)methanesulfonyl amide (3.5 g, 16 mM) was hydrogenated over Raney-Ni (0.5 g) in methanol at 50° C. and 70 psi for 4 hours. Then the catalyst was filtered off and washed with warm methanol. The combined filtrates were evaporated to give 2.83 g (95%) of (3-amino-phenyl)-methanesulfonamide. Then the catalyst was filtered off washed with warm methanol The combined filtrates were evaporated
Source ID: ord-30eace4a6bf24578a0f9337792d5d3b4Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (3-amino-phenyl)-methanesulfonamide (0.1 g, 0.54 mmol) and 4-chloro-6-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-pyrimidine (0.16 g, 0.0.57 mmol) in DMF (3 mL) was stirred at 90° C. till the reaction completion (TLC control), then evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel yielding (3-{6-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-pyrimidin-4-ylamino}-phenyl)-methanesulfonamide (Compound 83) as beige powder. evaporated in vacuo The resulting residue was purified by column chromatography on silica gel
Source ID: ord-cc7ab4dcabe94485bb9b4fe45fe736a9Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (3-amino-phenyl)-methanesulfonamide (0.18 g, 0.62 mmol) and 4-chloro-6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-pyrimidine (0.115 g, 0.62 mmol) in DMF (3 mL) was stirred at 80-90° C. till the reaction completion (TLC control), then evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel yielding (3-{6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-pyrimidin-4-ylamino}-phenyl)-methanesulfonamide (Compound 82) as white solid. evaporated in vacuo The resulting residue was purified by column chromatography on silica gel
Source ID: ord-ecadf2fd796146ed823dbc01d51eb61cConditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (3-amino-phenyl)-methanesulfonamide (0.16 g, 0.85 mmol) and 4-chloro-6-(2-methoxyphenyl)-pyrimidin-2-ylamine (0.2 g, 0.85 mmol) in DMF (5 mL) was stirred at 80-90° C. till the reaction completion (TLC control), then evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel yielding {3-[2-amino-6-(2-methoxy-phenyl)-pyrimidin-4-ylamino]-phenyl}-methanesulfonamide evaporated in vacuo The resulting residue was purified by column chromatography on silica gel
Source ID: ord-7ae01d16e73b4d3dbbb549bc0811dd19PubChem References
These sources are listed in the compound's public database record.
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