Trifluoroacetic acid → HCID 178428195, compound

HRID 1047579Notes

Reaction equation

HRID 1047579 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]=[CH:36][C:37]([N:39]3[CH2:44][CH2:43][CH:42]([CH3:45])[CH2:41][CH2:40]3)=[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:34][C:33]2[CH:35]=[CH:36][C:37]([N:39]3[CH2:40][CH2:41][CH:42]([CH3:45])[CH2:43][CH2:44]3)=[CH:38][C:32]=2[N:31]=1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178428193HCID 178428193, compound

Product 1

HCID 178428195HCID 178428195, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.432 mL, 5.61 mmol) was added to solution of 2,2-difluoro-N-(3-(5-(4-methylpiperidin-1-yl)-1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)cyclopropanecarboxamide (30 mg, 0.056 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 (20 mg) as an off-white solid. 1H NMR: (400 MHz, CD3OD): δ 8.48 (d, 1H, J=1.2 Hz), 7.43 (dd, 1H, J=1.2 and 8.8 Hz), 7.55 (m, 2H), 7.20 (d, 1H, J=2.0 Hz), 7.06 (dd, 1H, J=2.0 and 9.2 Hz), 3.59 (m, 2H), 2.73 (m, 3H), 2.13 (m, 1H), 1.89-1.77 (m, 3H), 1.53-1.37 (m, 3H), 1.00 (d, 3H, J=6.0 Hz); ESI-MS [M+H]+: 451.2.

Workup

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

Sources & evidence

ORD record
ord-e74af900e501431a85b875166017c636
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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