Trifluoroacetic acid → HCID 60203888, compound

HRID 2368188Notes

Reaction equation

HRID 2368188 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-f0b09c67a5514b0fb57c6c2e37f0f7e4
Source dataset
uspto-grants-2014_04
Patent number
US08703767B2

Reaction notes

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