Trifluoroacetic acid → HCID 71469140, compound

HRID 2368184Notes

Reaction equation

HRID 2368184 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[C:13]2[N:15](C3CCCCO3)[N:16]=[CH:17][C:12]2=[C:11]([C:24]2[CH:25]=[C:26]([NH:30][C:31](=[O:34])[CH:32]=[CH2:33])[CH:27]=[CH:28][CH:29]=2)[N:10]=1>C(Cl)Cl>[Cl:8][C:9]1[N:14]=[C:13]2[NH:15][N:16]=[CH:17][C:12]2=[C:11]([C:24]2[CH:25]=[C:26]([NH:30][C:31](=[O:34])[CH:32]=[CH2:33])[CH:27]=[CH:28][CH:29]=2)[N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86677518N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

Product 1

HCID 71469140HCID 71469140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroacetic acid (0.40 mL, 5.218 mmol) was added to a solution of N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide (20 mg, 0.052 mmol) in CH2Cl2 (4 mL) and the reaction mixture was stirred for 16 h at room temperature. The solvent was then 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, CDCl3): δ 8.72 (s, 1H), 8.59 (s, 1H), 8.01 (d, 1H, J=7.2 Hz), 7.82 (m, 1H), 7.57 (t, 1H, J=8.0 Hz), 6.43 (m, 2H), 5.80 (dd, 1H, J=2.8 and 8.8 Hz); ESI-MS: 300.10 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-01b68391f2334dde91f6926496ccb3e1
Source dataset
uspto-grants-2014_04
Patent number
US08703767B2

Reaction notes

Loading…