HCID 57655943, compound → HCID 57656610, compound

HRID 911685Notes

Reaction equation

HRID 911685 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:33])[NH:29][CH2:30][CH2:31][CH3:32])=[C:24]([F:34])[CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C>O1CCOCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:33])[NH:29][CH2:30][CH2:31][CH3:32])=[C:24]([F:34])[CH:23]=1

Participants

3

Reactant 1

HCID 57655943HCID 57655943, compound

Product 1

HCID 57656610HCID 57656610, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Use a method similar to the General Procedure 1-4 to deprotect 3-tert-butoxycarbonyl-7-chloro-6-(3-fluoro-4-propylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (33.1 mg, 0.83 mmol) in 1,4-dioxane (1 mL). Purify by SCX chromatography eluting with dichloromethane and dichloromethane/2M ammonia in methanol (1:1) to afford 7-Chloro-6-(3-fluoro-4-propylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a colorless oil (25.2 mg, 96%). MS (ES+) m/z: 390.1 (M+H)+. Use a method similar to the General Procedure 2-6, using 7-chloro-6-(3-fluoro-4-propylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (25 mg, 0.064 mmol) to provide the title compound as a white foam (31.4 mg, 91%). MS (ES+) m/z: 390.1 (M+H)+.

Workup

  1. customPurify by SCX chromatography
  2. washeluting with dichloromethane and dichloromethane/2M ammonia in methanol (1:1)

Sources & evidence

ORD record
ord-741b228a1845459f89d78e9650671f92
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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