Trifluoroacetic acid → N-(3-(6-((3-fluoro-4-morpholinophenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

HRID 2368181Notes

Reaction equation

HRID 2368181 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:21][C:22]2[N:27]=[C:26]3[N:28](C4CCCCO4)[N:29]=[CH:30][C:25]3=[C:24]([C:37]3[CH:38]=[C:39]([NH:43][C:44](=[O:47])[CH:45]=[CH2:46])[CH:40]=[CH:41][CH:42]=3)[N:23]=2)[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([NH:21][C:22]2[N:27]=[C:26]3[NH:28][N:29]=[CH:30][C:25]3=[C:24]([C:37]3[CH:38]=[C:39]([NH:43][C:44](=[O:47])[CH:45]=[CH2:46])[CH:40]=[CH:41][CH:42]=3)[N:23]=2)[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68388393N-(3-(6-((3-fluoro-4-morpholinophenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

Product 1

HCID 68388406N-(3-(6-((3-fluoro-4-morpholinophenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroacetic acid (0.283 mL, 3.68 mmol) was added to a solution of N-(3-(6-((3-fluoro-4-morpholinophenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide (20 mg, 0.037 mmol) in CH2Cl2 (5 mL), and the reaction mixture was stirred overnight at room temperature, after which the solvent was removed by vacuum. 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 8.72 (s, 1H), 8.34 (s, 1H), 8.01 (d, 1H, J=8.4 Hz), 7.94 (m, 1H), 7.73 (m, 1H), 7.54 (t, 1H, J=8.0 Hz), 7.41 (m, 1H), 7.01 (t, 1H, J=9.6 Hz), 6.44 (m, 2H), 5.81 (dd, 1H, J=2.4 & 9.6 Hz), 3.85 (m, 4H), 3.05 (m, 4H); ESI-MS: [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-2a51c607acc34464af7ad59f0c672a9b
Source dataset
uspto-grants-2014_04
Patent number
US08703767B2

Reaction notes

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