Trifluoroacetic acid → HCID 178521829, compound

HRID 1047562Notes

Reaction equation

HRID 1047562 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:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20](C1CCCCO1)[N:19]=[C:18]2[C:30]1[NH:34][C:33]2[CH:35]=[CH:36][C:37]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[CH:38][C:32]=2[N:31]=1)=[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:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[C:18]2[C:30]1[NH:34][C:33]2[CH:35]=[CH:36][C:37]([N:39]3[CH2:40][CH2:41][O:42][CH2:43][CH2:44]3)=[CH:38][C:32]=2[N:31]=1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178521727HCID 178521727, compound

Product 1

HCID 178521829HCID 178521829, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2.212 μL, 0.029 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-5-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 column chromatography (5% CH3OH/CH2Cl2) afforded the title compound (10 mg) as a yellow solid. 1H NMR: (400 MHz, CD3OD): δ 8.69 (d, 1H, J=1.2 Hz), 7.71 (d, 1H, J=9.2 Hz), 7.68 (d, 1H, J=8.8 Hz), 7.48 (dd, 1H, J=1.6 and 9.2 Hz), 7.35 (dd, 1H, J=1.6 and 9.6 Hz), 7.19 (m, 1H), 3.88 (m, 4H), 3.26 (m, 4H), 2.82-2.74 (m, 1H), 2.19-2.12 (m, 1H), 1.93-1.87 (m, 1H); ESI-MS: [M+H]+: 439.1.

Workup

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

Sources & evidence

ORD record
ord-49515f625aad417985f8c0c666906e4a
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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