Trifluoroacetic acid → HCID 68388374, compound

HRID 1500796Notes

Reaction equation

HRID 1500796 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[N:27]=[C:26]4[N:28](C5CCCCO5)[N:29]=[CH:30][C:25]4=[C:24]([C:37]4[CH:38]=[C:39]([NH:43][C:44](=[O:47])[CH:45]=[CH2:46])[CH:40]=[CH:41][CH:42]=4)[N:23]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1>C(Cl)Cl>[CH3:8][N:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]3[N:27]=[C:26]4[NH:28][N:29]=[CH:30][C:25]4=[C:24]([C:37]4[CH:38]=[C:39]([NH:43][C:44](=[O:47])[CH:45]=[CH2:46])[CH:40]=[CH:41][CH:42]=4)[N:23]=3)=[CH:19][CH:20]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68388399HCID 68388399, compound

Product 1

HCID 68388374HCID 68388374, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroacetic acid (0.15 mL, 1.86 mmol) was added to a solution of N-(3-(6-((4-(4-methylpiperazin-1-yl)phenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide (10 mg, 0.018 mmol) in CH2Cl2 (4 mL) and the reaction mixture was stirred for 16 h at room temperature, after which the solvent was removed in vacuo. The residue was purified by flash chromatography (6% CH3OH/CH2Cl2) to yield the title compound as an off white solid. 1H NMR (400 MHz, CD3OD): δ 8.67 (s, 1H), 8.31 (s, 1H), 7.99 (d, 1H, J=7.6 Hz), 7.75 (m, 3H), 7.54 (m, 1H), 6.99 (m, 2H), 6.46 (m, 2H), 5.81 (dd, 1H, J=2.4 Hz and 9.6 Hz), 3.17 (m, 4H), 2.64 (m, 4H), 2.35 (s, 3H); ESI-MS: 455.27 [M+H]+.

Workup

  1. customafter which the solvent was removed in vacuo
  2. customThe residue was purified by flash chromatography (6% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-e276dee60e8e40e484b4a2ae5e0364a2
Source dataset
uspto-grants-2015_12
Patent number
US09206176B2

Reaction notes

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