Trifluoroacetic acid → HCID 178521830, compound

HRID 1047564Notes

Reaction equation

HRID 1047564 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1([F:48])[CH2:14][CH2:13][CH:12]([C:15]([NH:17][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23](C2CCCCO2)[N:22]=[C:21]3[C:33]2[NH:37][C:36]3[CH:38]=[CH:39][C:40]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)=[CH:41][C:35]=3[N:34]=2)=[O:16])[CH2:11][CH2:10]1>C(Cl)Cl>[F:48][C:9]1([F:8])[CH2:10][CH2:11][CH:12]([C:15]([NH:17][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][N:22]=[C:21]3[C:33]2[NH:37][C:36]3[CH:38]=[CH:39][C:40]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)=[CH:41][C:35]=3[N:34]=2)=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178521728HCID 178521728, compound

Product 1

HCID 178521830HCID 178521830, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.082 mL, 1.063 mmol) was added to a solution of 4,4-difluoro-N-(3-(5-morpholino-1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)cyclohexanecarboxamide (6 mg, 10.63 μmol) in CH2Cl2 (5 mL). The reaction mixture was stirred overnight at room temperature, and the solvent was removed in vacuo. Purification by flash column chromatography (5% CH3OH/CH2Cl2) afforded the title compound (4 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 8.46 (s, 1H), 7.69 (m, 1H), 7.57 (m 2H), 7.18 (d, 1H, J=1.6 Hz), 7.07 (dd, 1H, J=2.0 and 8.8 Hz), 3.88 (m, 4H), 3.18 (m, 4H), 2.55 (m, 1H), 2.17 (m, 2H), 2.01 (m, 2H), 1.96-1.83 (m, 4H); ESI-MS [M+H]+: 481.28.

Workup

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

Sources & evidence

ORD record
ord-c0571065551246e2b77cc0b62be5e66e
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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