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C1CNCC(CN1)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1,4-diazepan-6-ol |
|---|---|
| IUPAC Name | — |
| CAS Number | 28795-81-5 |
| Database ID | 21114275 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1,4-diazepan-6-ol (CAS 28795-81-5) 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 21114275
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-fee824815110420bb8adf17aa2ecc6c7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8e6c0e0536ac45e7a858a8d0a51227c2Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (5-benzenesulfinylmethyl-pyrrolo[2,1-f][1,2,4]triazin-4-yl)-[1-(3-fluoro-benzyl)-1H-indazol-5-yl]-amine (397 mg, 0.8 mmole) and [1,4]diazepan-6-ol (417 mg, 4.5 equiv, Saari et al., J. Org. Chem., 1971, 36, 1711) in dry DMSO (1.5 mL) in a sealed tube was heated at 140° C. for 11 hr. This was diluted with DCM (150 ml), washed with water and dried (Na2SO4). Removal of the solvent followed by radial chromatography (4 mm silica gel plate; gradient elution with DCM containing 0 to 3% of a 2N NH3 solution in MeOH) gave the title compound as a solid (242 mg, 62%), MS: 487 (M+H)+; HPLC Ret Time: 0.96 min (Xterra S7 3.0×50 mm S7 C18 column, 2 min gradient, 5 ml/min). The racemic material could be separated on a Chiralpak AD 4.6×250 mm column, eluting with 0.05% diethylamine in EtOH for 25 min with a flow rate of 0.7 mL/min) The S and R enantiomers had retention times of 16.20 and 18.90 min respectively. The R enantiomer was synthesized as outlined below. washed with water dried (Na2SO4) Removal of the solvent gradient elution with DCM containing 0 to 3% of a 2N NH3 solution in MeOH)
Source ID: ord-172bf42307aa4835a0d0ed089692635dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-bromo-2-fluoro-6-iodopyridine (1.00 g, 3.4 mmol), 1,4-diazepan-6-ol (510 mg, 4.4 mmol), and DIPEA (2 mL) in EtOH (6 mL) in a sealed tube was stirred at 100° C. for 20 hours. The reaction mixture was concentrated under reduced pressure to give a residue (1.18 g), which was used for the next step without further purification. MS (ESI) m/z: 398 [M+H]+. The reaction mixture was concentrated under reduced pressure
Source ID: ord-430b14e236a94fdb91f5f889ce24ada9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedures as described in Example 124 and starting with 1,4-diazepan-6-ol, 3,5-dibromo-1-methylpyrazin-2(1H)-one, 6-chloro-1H-pyrazolo[4,3-c]pyridine, and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 254 was obtained as a yellow solid (80 mg, 7.2%) over five steps. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.09 (s, 1H), 8.43 (s, 1H), 8.30 (s, 1H), 8.29 (s, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 4.91 (s, 1H), 4.49 (m, 1H), 3.92 (m, 1H), 3.89 (s, 3H), 3.70-3.71 (m, 2H), 3.51 (s, 3H), 2.99-3.02 (m, 1H), 2.90-2.91 (m, 1H), 2.74-2.86 (m, 2H); MS (ESI) m/z: 422 [M+H]+.
Source ID: ord-7433d3c2b28442f69cffb0e1ccadbe21Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 2-bromo-6-fluoropyridine (845 mg, 4.83 mmol) and 1,4-diazepan-6-ol (560 mg, 4.83 mmol) in EtOH (20 mL) was added DIPEA (5 mL). The reaction mixture was heated at 100° C. for 15 hours, which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude material was used in the next step without further purification. MS (ESI) m/z: 272 [M+H]+. After completion of the reaction, it was concentrated under reduced pressure The crude material was used in the next step without further purification
Source ID: ord-4a5ad81b49fa410da081a9482bd7ec5fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedures as described in Example 124 and starting with 1,4-diazepan-6-ol, 2-bromo-6-fluoropyridine, 6-chloro-1H-pyrazolo[4,3-c]pyridine, and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 231 was obtained as a yellow solid (43 mg, 23.5%) over six steps. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.09 (s, 1H), 8.65 (s, 1H), 8.44 (s, 1H), 8.25 (s, 1H), 7.98 (s, 1H), 7.63-7.68 (m, 1H), 7.14-7.16 (d, J=12.5 Hz, 1H), 6.61-6.64 (d, J=14 Hz, 1H), 4.10-4.14 (m, 1H), 3.86-3.91 (m, 6H), 3.55-3.66 (m, 2H), 2.98-3.04 (m, 3H), 2.84-2.90 (m, 1H), 2.69-2.71 (m, 1H); MS (ESI) m/z: 391 [M+H]+.
Source ID: ord-96929d1b433b4469862c2d7ace374d4cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedures as described in Example 124 and starting with 1,4-diazepan-6-ol, 2-bromo-6-fluoropyridine, 6-chloro-1H-pyrazolo[4,3-c]pyridine, and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 229 was obtained as a yellow solid (40 mg, 24.1%) over six steps. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.09 (s, 1H), 8.65 (s, 1H), 8.44 (s, 1H), 8.25 (s, 1H), 7.98 (s, 1H), 7.63-7.68 (m, 1H), 7.14-7.16 (d, J=12.5 Hz, 1H), 6.61-6.64 (d, J=14 Hz, 1H), 4.10-4.14 (m, 1H), 3.86-3.91 (m, 6H), 3.55-3.66 (m, 2H), 2.98-3.04 (m, 3H), 2.84-2.90 (m, 1H), 2.69-2.71 (m, 1H); MS (ESI) m/z: 391 [M+H]+.
Source ID: ord-bc9c6952d7d046b8a48fb5195c6b113bConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-bromo-6-fluoropyridine (477 mg, 2.7 mmol), 1,4-diazepan-6-ol (350 mg, 3 mmol), and DIPEA (1.94 g, 15 mmol) in ethanol (10 mL) was heated at 100° C. for 16 hours. After it was cooled, the reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc (100 mL) and washed with brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 1-(6-bromopyridin-2-yl)-1,4-diazepan-6-ol as a colorless oil (400 mg, 48.9%). MS (ESI) m/z: 272 [M+H]+. After it was cooled the reaction mixture was concentrated under reduced pressure The residue was diluted with EtOAc (100 mL) washed with brine The organic layer was dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-4a05fc6b800647e6bfba96bdba62fac7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedures as described in EXAMPLE 8 and starting with 1-(6-fluoropyridin-2-yl)-6-(5-(oxetan-3-yl)pyridin-3-yl)-1H-pyrazolo[4,3-c]pyridine and 1,4-diazepan-6-ol, 116 was obtained as an off-white solid (7.2 mg, 6%). 1H NMR (400 MHz, DMSO) δ 9.35-9.29 (s, 1H), 9.23-9.16 (dd, J=8.9, 2.0 Hz, 1H), 9.11-9.04 (d, J=8.6 Hz, 1H), 8.77-8.62 (m, 2H), 8.55-8.46 (dd, J=15.4, 8.6 Hz, 1H), 7.74-7.67 (t, J=8.1 Hz, 1H), 7.21-7.16 (d, J=7.7 Hz, 1H), 6.77-6.68 (dd, J=8.5, 2.9 Hz, 1H), 5.69-5.45 (d, J=72.4 Hz, 1H), 5.06-5.00 (dd, J=8.1, 6.2 Hz, 1H), 4.81-4.70 (dd, J=13.5, 6.7 Hz, 2H), 4.48-4.40 (m, 1H), 4.06-3.85 (dd, J=32.4, 13.9 Hz, 3H), 3.74-3.53 (m, 2H), 3.00-2.93 (d, J=2.3 Hz, 2H), 2.83-2.77 (dd, J=13.8, 3.8 Hz, 1H), 2.70-2.62 (dd, J=13.2, 6.0 Hz, 1H); MS (ESI) m/z: 444.2 [M+H]+
Source ID: ord-e63e13aef72047c49702b4240684b267Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedures as described in EXAMPLE 8 and starting with 6-(5-cyclopropylpyridin-3-yl)-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine and 1,4-diazepan-6-ol, 115 was obtained as an off-white solid (25.1 mg, 17%). 1H NMR (400 MHz, DMSO) δ 9.31-9.27 (s, 1H), 9.07-9.00 (dd, J=16.3, 6.5 Hz, 2H), 8.65-8.59 (d, J=5.6 Hz, 1H), 8.48-8.44 (t, J=2.8 Hz, 1H), 8.09-8.03 (t, J=2.0 Hz, 1H), 7.73-7.67 (t, J=8.1 Hz, 1H), 7.20-7.14 (d, J=7.7 Hz, 1H), 6.73-6.68 (d, J=8.5 Hz, 1H), 4.82-4.73 (s, 1H), 4.03-3.87 (m, 3H), 3.74-3.57 (m, 2H), 3.02-2.93 (t, J=5.4 Hz, 2H), 2.87-2.75 (dd, J=13.8, 3.8 Hz, 1H), 2.70-2.60 (dd, J=13.8, 5.9 Hz, 1H), 2.15-2.03 (m, 1H), 1.10-1.02 (m, 2H), 0.92-0.82 (m, 2H); MS (ESI) m/z: 428.2 [M+H]+
Source ID: ord-5798b68297134e059cd572acaa229d75Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedures as described in EXAMPLE 8 and starting with 6-(5-ethylpyridin-3-yl)-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine and 1,4-diazepan-6-ol, 106 was obtained as an off-white solid (49.4 mg, 12%). MS (ESI) m/z: 416.1 [M+H]+
Source ID: ord-52908b37ccd9450c8a307710dde7efcdPubChem References
These sources are listed in the compound's public database record.
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