Trifluoroacetic acid → HCID 136232546, compound

HRID 1047580Notes

Reaction equation

HRID 1047580 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1([F:45])[CH2:11][CH:10]1[C:12]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17]([C:30]1[NH:34][C:33]3[CH:35]=[CH:36][C:37]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[CH:38][C:32]=3[N:31]=1)=[N:18][N:19]2C1CCCCO1)=[O:13]>C(Cl)Cl>[F:45][C:9]1([F:8])[CH2:11][CH:10]1[C:12]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17]([C:30]1[NH:31][C:32]3[CH:38]=[C:37]([N:39]4[CH2:40][CH2:41][O:42][CH2:43][CH2:44]4)[CH:36]=[CH:35][C:33]=3[N:34]=1)=[N:18][NH:19]2)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178521850HCID 178521850, compound

Product 1

HCID 136232546HCID 136232546, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (327 mg, 2.87 mmol) was added to solution of 2,2-difluoro-N-(3-(5-morpholino-1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)cyclopropane carboxamide (15 mg, 0.029 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred overnight at room temperature, and then the solvent was removed in vacuo. Purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound (8 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 8.18 (d, 1H, J=8.0 Hz), 7.49 (d, 1H, J=8.8 Hz), 7.35 (m, 1H), 7.25 (d, 1H, J=8.0 Hz), 7.18 (s, 1H), 7.09 (d, 1H, J=7.6 Hz), 3.89 (m, 4H), 3.22 (m, 4H), 3.08-3.01 (m, 1H), 2.21-2.15 (m, 1H), 1.96 (m, 1H); ESI-MS [M+H]+: 439.1.

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification by flash chromatography (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-d168d097f74a48ee853ca8d856add411
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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