4,5-Dihydro-1-methoxy-3H-2-benzazepine → HCID 86614849, compound

HRID 1863959Notes

Reaction equation

HRID 1863959 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=1[F:23])[CH2:9][C:10]([NH:12][NH2:13])=O)([CH3:4])([CH3:3])[CH3:2].CO[C:27]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[CH2:31][CH2:30][CH2:29][N:28]=1>COCCO>[N:13]1[N:12]=[C:10]([CH2:9][C@H:8]([NH:7][C:6](=[O:24])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=2[F:23])[N:28]2[CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:27]=12

Participants

4

Reactant 2

HCID 552773564,5-Dihydro-1-methoxy-3H-2-benzazepine2×HCID 57973796HCID 57973796, compound2×

Product 1

HCID 86614849HCID 86614849, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 90 mg (0.26 mmol) of tert-butyl [(1R)-3-hydrazino-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate (Intermediate 4), 45.5 mg (0.26 mmol) of 1-methoxy-4,5-dihydro-3H-2-benzazepine (Intermediate 10), and 3.5 mL of 2-methoxyethanol was stirred at reflux for 43 h. The cooled solution was concentrated, and the residue was purified by preparative HPLC (C18 reverse phase column, 20-90% acetonitrile in water containing 0.05% trifluoroacetic acid) to give the title compound as a colorless oil. LC-MS 473 (M+1).

Workup

  1. temperatureat reflux for 43 h
  2. concentrationThe cooled solution was concentrated
  3. customthe residue was purified by preparative HPLC (C18 reverse phase column, 20-90% acetonitrile in water containing 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-3f8ae9fe68774c809e1fc69165c5d09a
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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