Trifluoroacetic acid → N-(3-(1H-benzo[d]imidazol-2-yl)-1H-indazol-5-yl)-2,2-difluorocyclopropanecarboxamide

HRID 1047540Notes

Reaction equation

HRID 1047540 reaction equation
C(O)(C(F)(F)F)=O.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([CH:29]3[CH2:31][C:30]3([F:33])[F:32])=[O:28])[CH:24]=2)[N:19](C2CCCCO2)[N:18]=1>C(Cl)Cl>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([CH:29]3[CH2:31][C:30]3([F:33])[F:32])=[O:28])[CH:24]=2)[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136352252N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-2,2-difluorocyclopropanecarboxamide

Product 1

HCID 136232544N-(3-(1H-benzo[d]imidazol-2-yl)-1H-indazol-5-yl)-2,2-difluorocyclopropanecarboxamideYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.1 mL, 1.587 mmol) was added to a solution of N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-2,2-difluorocyclopropanecarboxamide (10 mg, 0.023 mmol) in CH2Cl2 (4 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuo. Purification by flash chromatography (6% CH3OH/CH2Cl2) afforded the title compound (6 mg). 1H NMR (400 MHz, CD3OD): δ 8.69 (s, 1H), 7.82 (m, 2H), 7.70 (d, 1H, J=8.8 Hz), 7.56-7.50 (m, 3H), 2.82-2.73 (m, 1H), 2.21-2.12 (m, 1H), 1.94-1.85 (m, 1H); ESI-MS [M+H]+: 354.2.

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification by flash chromatography (6% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-5cad41ad2e9646ab9d90b4b850df8c37
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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