Trifluoroacetic acid → HCID 178521827, compound

HRID 1047556Notes

Reaction equation

HRID 1047556 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1([F:46])[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]=[C:36]([CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[CH:37]=[CH:38][C:32]=2[N:31]=1)=[O:13]>C(Cl)Cl>[F:46][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:31][C:32]2[CH:38]=[CH:37][C:36]([CH2:39][N:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)=[CH:35][C:33]=2[N:34]=1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136352260HCID 136352260, compound

Product 1

HCID 178521827HCID 178521827, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.15 mL, 1.86 mmol) was added to solution of 2,2-difluoro-N-(3-(6-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)cyclopropane carboxamide (10 mg, 0.018 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred overnight at room temperature, and then the solvent was removed by vacuum. Purification by flash column chromatography (5% CH3OH/CH2Cl2) afforded the title compound (4 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 8.49 (d, 1H, J=1.6 Hz), 7.69 (dd, 1H, J=1.6 and 8.8 Hz), 7.63-7.58 (m, 3H), 7.28 (m, 1H), 3.71 (m, 4H), 3.67 (m, 2H), 2.79-2.70 (m, 1H), 2.52 (m, 4H), 2.36-2.32 (m, 1H), 2.15-2.06 (m, 1H); ESI-MS [M+H]+: 453.2.

Workup

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

Sources & evidence

ORD record
ord-bd700f08d6c24f17b4b7fb289633a917
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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