No renderable structure data available
CC(C)(C1CNC1)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-(azetidin-3-yl)propan-2-ol |
|---|---|
| IUPAC Name | — |
| CAS Number | 1257293-78-9 |
| Database ID | 53249204 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-(azetidin-3-yl)propan-2-ol (CAS 1257293-78-9) 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 53249204
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
8 reactions · 8 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b192e643a5e8413d8f0c49d11dea7292Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared in an analogous fashion to that described in Stage 128.1 using 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2) and 2-azetidin-3-yl-propan-2-ol (WO2010138589) to afford an off-white crystalline product. HPLC (Condition 4) tR=5.84 min, UPLC-MS (Condition 7) m/z=474.1 [M+H]+. to afford an off-white crystalline product
Source ID: ord-fbd10bcafc01443d90cc29675f17e9a2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared in an analogous fashion to that described in Stage 128.1 using 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2) and 2-azetidin-3-yl-propan-2-ol (WO2010138589) to afford an off-white crystalline product. HPLC (Condition 4) tR=5.84 min, UPLC-MS (Condition 7) m/z=474.1 [M+H]+. to afford an off-white crystalline product
Source ID: ord-fbd10bcafc01443d90cc29675f17e9a2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-(2-methylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (0.075 g, 0.20 mmol), 2-azetidin-3-ylpropan-2-ol (0.023 g, 0.20 mmol) in DCE (2 mL), trimethoxymethane (0.215 mL, 2 mmol) and acetic acid (0.012 mL, 0.2 mmol) was stirred for 1 h at room temperature. Sodium triacetoxyborohydride (0.042 g, 0.2 mmol) was added and the reaction mixture was stirred for 18 h at room temperature. The reaction mixture was partitioned between DCM and water, and the organic layer was separated, washed with brine, dried over sodium sulphate and concentrated. The residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 10:90) to give 315 as an off-white solid (0.020 g, 23%). LCMS (Method G): RT=5.61 min, [M+H]+ 477.2. 1H NMR (CDCl3, 400 MHz) δ 8.11-8.07 (m, 1 H); 7.72-7.69 (m, 1 H); 7.35-7.26 (m, 2 H); 4.42-4.31 (m, 4 H); 3.89-3.82 (m, 11 H); 3.62-3.12 (m, 2H); 2.94 (s, 3 H); 2.70-2.55 (m, 1 H); 1.18 (s, 6 H) the reaction mixture was stirred for 18 h at room temperature The reaction mixture was partitioned between DCM and water the organic layer was separated washed with brine dried over sodium sulphate concentrated The residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 10:90)
Source ID: ord-91c3d75b6db24fae9f134737ed9231beConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde (300 mg, 1.01 mmol) in DCE (20 mL) was added 2-azetidin-3-ylpropan-2-ol (118 mg, 1.02 mmol), trimethyl orthoformate (1.11 mL, 10.14 mmol) and acetic acid (0.06 mL, 1.01 mmol). The reaction mixture was stirred at room temperature for 6 h, sodium triacetoxyborohydride (323 mg, 1.52 mmol) was added and the resulting mixture stirred for a further 18 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, the cartridge was washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography (Si—PCC, 0-10% MeOH in DCM) to give the title compound as a pale yellow oil (90 mg, 23%). LCMS (Method A): RT=2.37 min, [M+H]+ 395.2 the resulting mixture stirred for a further 18 h the cartridge was washed with MeOH the desired product eluted with 2 M NH3 in MeOH The resulting residue was purified by column chromatography (Si—PCC, 0-10% MeOH in DCM)
Source ID: ord-91e9b48b1f0b4580807a4e51b114359fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-(2-methylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (0.075 g, 0.20 mmol), 2-azetidin-3-ylpropan-2-ol (0.023 g, 0.20 mmol) in DCE (2 mL), trimethoxymethane (0.215 mL, 2 mmol) and acetic acid (0.012 mL, 0.2 mmol) was stirred for 1 h at room temperature. Sodium triacetoxyborohydride (0.042 g, 0.2 mmol) was added and the reaction mixture was stirred for 18 h at room temperature. The reaction mixture was partitioned between DCM and water, and the organic layer was separated, washed with brine, dried over sodium sulphate and concentrated. The residue was purified by flash chromatography (Si—PPC, MEOH:DCM, gradient 0:100 to 10:90) to give 315 as an off-white solid (0.020 g, 23%). LCMS (Method G): RT=5.61 min, [M+H]+ 477.2. 1H NMR (CDCl3, 400 MHz) δ 8.11-8.07 (m, 1 H); 7.72-7.69 (m, 1 H); 7.35-7.26 (m, 2 H); 4.42-4.31 (m, 4 H); 3.89-3.82 (m, 11 H); 3.62-3.12 (m, 2 H); 2.94 (s, 3 H); 2.70-2.55 (m, 1H); 1.18 (s, 6 H) the reaction mixture was stirred for 18 h at room temperature The reaction mixture was partitioned between DCM and water the organic layer was separated washed with brine dried over sodium sulphate concentrated The residue was purified by flash chromatography (Si—PPC, MEOH:DCM, gradient 0:100 to 10:90)
Source ID: ord-8a51235a40a8432fa82d386397b15dd6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde (300 mg, 1.01 mmol) in DCE (20 mL) was added 2-azetidin-3-ylpropan-2-ol (118 mg, 1.02 mmol), trimethyl orthoformate (1.11 mL, 10.14 mmol) and acetic acid (0.06 mL, 1.01 mmol). The reaction mixture was stirred at room temperature for 6 h, sodium triacetoxyborohydride (323 mg, 1.52 mmol) was added and the resulting mixture stirred for a further 18 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, the cartridge was washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography (Si—PCC, 0-10% MeOH in DCM) to give the title compound as a pale yellow oil (90 mg, 23%). LCMS (Method A): RT=2.37 min, [M+H]+ 395.2 the resulting mixture stirred for a further 18 h the cartridge was washed with MeOH the desired product eluted with 2 M NH3 in MeOH The resulting residue was purified by column chromatography (Si—PCC, 0-10% MeOH in DCM)
Source ID: ord-d78e8cf87ff1415d91e14f92e30f4ef5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared in an analogous fashion to that described in Stage 128.1 using 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2) and 2-azetidin-3-yl-propan-2-ol (WO2010138589) to afford an off-white crystalline product. HPLC (Condition 4) tR=5.84 min, UPLC-MS (Condition 7) m/z=474.1 [M+H]+. to afford an off-white crystalline product
Source ID: ord-fbd10bcafc01443d90cc29675f17e9a2PubChem References
These sources are listed in the compound's public database record.
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