Trifluoroacetic acid → N-{[1-(4-Amino-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide TFA salt

HRID 2188582Notes

Reaction equation

HRID 2188582 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:17][CH:16]([NH:18][C:19](=[O:34])[CH2:20][NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH2:15]2)[CH2:10][CH2:9]1)(C)(C)C.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>C(Cl)Cl>[OH:42][C:36]([C:38]([F:41])([F:40])[F:39])=[O:37].[NH2:7][CH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:17][CH:16]([NH:18][C:19]([CH2:20][NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=3)=[O:34])[CH2:15]2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59541119{4-{3-[2-(3-Trifluoromethyl-benzoylamino)-acetylamino]-azetidin-1-yl}-cyclohexyl)-carbamic acid tert-butyl ester

Product 1

HCID 86646662N-{[1-(4-Amino-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide TFA salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {4-{3-[2-(3-trifluoromethyl-benzoylamino)-acetylamino]-azetidin-1-yl}-cyclohexyl)-carbamic acid tert-butyl ester (less polar isomer, as prepared in the previous step 5.6 g, 11.2 mmol) in DCM 10 mL and TFA (10 mL) was stirred for 4 hours at room temperature. The solvent was removed and the residue was dried in vacuo to afford the title compound as colorless oil.

Workup

  1. customThe solvent was removed
  2. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-2b333eefa172451c81a4bb1a0f4e81ba
Source dataset
uspto-grants-2012_12
Patent number
US08324186B2

Reaction notes

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