Trifluoroacetic acid → HCID 178429877, compound

HRID 1047574Notes

Reaction equation

HRID 1047574 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][O:42][CH:41]([CH3:45])[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[CH2:44][CH2:43][O:42][CH:41]([CH3:45])[CH2:40]3)=[CH:38][C:32]=2[N:31]=1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178429875HCID 178429875, compound

Product 1

HCID 178429877HCID 178429877, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.215 mL, 2.80 mmol) was added to solution of 2,2-difluoro-N-(3-(5-(2-methylmorpholino)-1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)cyclopropanecarboxamide (15 mg, 0.028 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 (9 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 8.44 (d, 1H, J=0.8 Hz), 7.64 (dd, 1H, J=1.6 and 8.8 Hz), 7.58-7.54 (m, 2H), 7.17 (d, 1H, J=1.6 Hz), 7.04 (dd, 1H, J=2.0 and 8.8 Hz), 3.99 (m, 1H), 3.82 (m, 2H), 3.52 (m, 1H), 3.44 (m, 1H), 2.84-2.70 (m, 2H), 2.47 (m, 1H), 2.12 (m, 1H), 1.85 (m, 1H), 1.24 (d, 3H, J=6.0 Hz); ESI-MS [M+H]+: 453.1.

Workup

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

Sources & evidence

ORD record
ord-3af1416b3c3d4ade96c7aee5c639d7d2
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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