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

HRID 1364133Notes

Reaction equation

HRID 1364133 reaction equation
[CH3:1][N:2]([CH3:28])[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][N:2]([CH3:28])[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 669309031,1-Dimethylethyl 2-{4-[(dimethylamino)carbonyl]phenyl}-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate

Product 1

HCID 66930795N,N-Dimethyl-4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 2-{4-[(dimethylamino)carbonyl]phenyl}-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 41) (194 mg, 0.50 mmol) in dichloromethane (14 ml) was added trifluoroacetic acid (7 ml). The resulting mixture was stirred at room temperature, under argon, for 2 hours and then diluted with methanol. Reaction was purified by SCX, eluting with methanol and then 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo. Resulting crude product was purified further by column chromatography on silica gel, eluting with a mixture of 2M ammonia in methanol/dichloromethane (0-3%) to afford the title compound (D42). MS (ES+) m/e 285 [M+H]+.

Workup

  1. customReaction
  2. customwas purified by SCX
  3. washeluting with methanol
  4. customsolvent evaporated in vacuo
  5. customResulting crude product
  6. customwas purified further by column chromatography on silica gel
  7. washeluting with a mixture of 2M ammonia in methanol/dichloromethane (0-3%)

Sources & evidence

ORD record
ord-b4aabd4d991740e78a0d41f71aa8d897
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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