HCID 86629670, compound → HCID 86629668, compound

HRID 911671Notes

Reaction equation

HRID 911671 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1[N:19]([C:21]1[CH:35]=[CH:34][C:24]2[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:26][S:27][C:23]=2[CH:22]=1)[CH3:20]>N.CO>[ClH:1].[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[N:19]([C:21]1[CH:35]=[CH:34][C:24]2[C:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:26][S:27][C:23]=2[CH:22]=1)[CH3:20]

Participants

4

Reactant 1

HCID 86629670HCID 86629670, compound

Product 1

HCID 86629668HCID 86629668, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

Use a procedure similar to General Procedure 1-1 to deprotect 7-chloro-6-(3-phenyl-benzothiophen-6-yl-methylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (234 mg, 0.45 mmol) in 7M ammonia in methanol (20 mL). Purify by reverse phase HPLC (Vydac C18 5×25 cm, 30% to 100% acetonitrile in 0.1% TFA-water solution). Recover the free base by SCX chromatography and form the salt according to General Procedure 2-3 to obtain the title compound (38 mg, 17%). HRMS (ES+) m/z: 419.1340 (M+H)+.

Workup

  1. customPurify by reverse phase HPLC (Vydac C18 5×25 cm, 30% to 100% acetonitrile in 0.1% TFA-water solution)
  2. customRecover the free base by SCX chromatography
  3. customform the salt

Sources & evidence

ORD record
ord-733fa2fb28894deebe468eea9b386c09
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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