Trifluoroacetic acid → N-Methyl-4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide

HRID 1364120Notes

Reaction equation

HRID 1364120 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:20]=[C:19]3[C:13]([CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18]3)=[N:12]2)=[CH:7][CH:6]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl.CO>[CH3:1][NH:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:20]=[C:19]3[C:13]([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)=[N:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669307901,1-Dimethylethyl 2-{4-[(methylamino)carbonyl]phenyl}-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate

Product 1

HCID 66930754N-Methyl-4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 2-{4-[(methylamino)carbonyl]phenyl}-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (184 mg, 0.50 mmol; may be prepared as described in Description 24) in dichloromethane (2 ml) was treated with trifluoroacetic acid (2 ml). The mixture was stirred at room temperature for 2 hours. The mixture was diluted with methanol and passed down a SCX cartridge eluting with methanol and then a 2M solution of ammonia in methanol. The basic fractions were combined and evaporated to afford the title compound (D25); MS (ES+) m/e 271 [M+H]+.

Workup

  1. washeluting with methanol
  2. customevaporated

Sources & evidence

ORD record
ord-96ba3f9a18594e9b992f6c45839f6d72
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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