Trifluoroacetic acid → HCID 136232556, compound

HRID 1047581Notes

Reaction equation

HRID 1047581 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:23]=[C:22]2[C:18]([C:19]([C:30]3[NH:34][C:33]4[CH:35]=[CH:36][C:37]([N:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)=[CH:38][C:32]=4[N:31]=3)=[N:20][N:21]2C2CCCCO2)=[CH:17][CH:16]=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:23]=[C:22]2[C:18]([C:19]([C:30]3[NH:31][C:32]4[CH:38]=[C:37]([N:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)[CH:36]=[CH:35][C:33]=4[N:34]=3)=[N:20][NH:21]2)=[CH:17][CH:16]=1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178521745HCID 178521745, compound

Product 1

HCID 136232556HCID 136232556, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (546 mg, 4.78 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-6-yl)cyclopropan-ecarboxamide (25 mg, 0.048 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 (11 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 8.28 (d, 1H, J=1.2 Hz), 8.19 (d, 1H, J=8.8 Hz), 7.61 (d, 1H, J=9.2 Hz), 7.33 (dd, 1H, J=1.6 and 8.8 Hz), 7.25 (dd, 1H, J=2.0 and 8.8 Hz), 7.13 (s, 1H), 3.86 (m, 4H), 3.21 (m, 4H), 2.78-2.70 (m, 1H), 2.14 (m, 1H), 1.90-1.84 (m, 1H); ESI-MS [M+H]+: 439.1.

Workup

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

Sources & evidence

ORD record
ord-06852dc2aacd4542978b106058b0f394
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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