Trifluoroacetic acid → HCID 60203888, compound

HRID 1500798Notes

Reaction equation

HRID 1500798 reaction equation
FC(F)(F)C(O)=O.[O:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[C:25]4[N:27](C5CCCCO5)[N:28]=[CH:29][C:24]4=[C:23]([C:36]4[CH:37]=[C:38]([NH:42][C:43](=[O:46])[CH:44]=[CH2:45])[CH:39]=[CH:40][CH:41]=4)[N:22]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1>C(Cl)Cl>[O:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]3[N:26]=[C:25]4[NH:27][N:28]=[CH:29][C:24]4=[C:23]([C:36]4[CH:37]=[C:38]([NH:42][C:43](=[O:46])[CH:44]=[CH2:45])[CH:39]=[CH:40][CH:41]=4)[N:22]=3)=[CH:18][CH:19]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86677519HCID 86677519, compound

Product 1

HCID 60203888HCID 60203888, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroacetic acid (0.220 mL, 2.85 mmol) was added to a solution of N-(3-(6-((4-morpholinophenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide (15 mg, 0.029 mmol) in CH2Cl2 (5 mL) and the reaction mixture was stirred overnight at room temperature, after which the solvent was removed in vacuo. The residue was purified by flash column chromatography (5% CH3OH/CH2Cl2) to yield the title compound as a solid. 1H NMR (400 MHz, CD3OD): δ 8.71 (s, 1H), 7.32 (s, 1H), 7.99 (m, 1H), 7.74 (m, 3H), 7.54 (m, 1H), 7.00 (m, 2H), 6.48-6.43 (m, 2H), 5.82 (dd, 1H, J=2.4 and 9.6 Hz), 3.85 (m, 4H), 3.12 (m, 4H): ESI-MS: 442.27 [M+H]+.

Workup

  1. customafter which the solvent was removed in vacuo
  2. customThe residue was purified by flash column chromatography (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-3af5a2f4c5fd4f38ab6a21e32ab2023f
Source dataset
uspto-grants-2015_12
Patent number
US09206176B2

Reaction notes

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