Hydrochloric Acid → HCID 16062559, compound

HRID 1670543Notes

Reaction equation

HRID 1670543 reaction equation
Cl.C(OC([N:9]1[CH2:15][CH2:14][C:13]2[C:16]([CH2:21][NH:22][C:23]3[CH:28]=[CH:27][C:26]([C:29](=[O:38])[NH:30][CH:31]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:25][CH:24]=3)=[C:17]([Cl:20])[CH:18]=[CH:19][C:12]=2[CH2:11][CH2:10]1)=O)(C)(C)C>CCOC(C)=O.CO>[Cl:20][C:17]1[CH:18]=[CH:19][C:12]2[CH2:11][CH2:10][NH:9][CH2:15][CH2:14][C:13]=2[C:16]=1[CH2:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:38])[NH:30][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67337338HCID 67337338, compound

Product 1

HCID 16062559HCID 16062559, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
40 °C

Procedure

Add hydrogen chloride into a mixture of 3-tert-butoxycarbonyl-7-chloro-6-[(4-cycloheptylcarbamoyl-phenylamino)-methyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (590 mg, 1.12 mmol) in EtOAc/methanol (1:1, 60 mL) until the mixture is saturated. Stir for 1 h at 40° C. and concentrate in vacuo. Purify the residue by SCX chromatography to obtain 7-chloro-6-[(4-cycloheptylcarbamoyl-phenylamino)-methyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (450 mg, 1.06 mmol). Use a method similar to the General Procedure 2-1 to obtain the title compound as an off-white solid (560 mg, 92%). MS (ES+) m/z: 426 (M+H)+.

Workup

  1. concentrationconcentrate in vacuo
  2. customPurify the residue by SCX chromatography

Sources & evidence

ORD record
ord-ce0cf14073cd48558d774647725f2ecf
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

Loading…