3-(Trifluoromethyl)phenyl isocyanate → HCID 45380788, compound

HRID 2365755Notes

Reaction equation

HRID 2365755 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[N:12][C:13]=2[NH2:15])[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:7]=1.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:29]=[C:30]([N:34]=[C:35]=[O:36])[CH:31]=[CH:32][CH:33]=1>>[NH2:15][C:13]1[N:12]=[CH:11][N:10]=[C:9]2[N:8]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:7]=[C:6]([CH2:5][C:4]3[CH:3]=[C:2]([NH:1][C:35]([NH:34][C:30]4[CH:31]=[CH:32][CH:33]=[C:28]([C:27]([F:26])([F:37])[F:38])[CH:29]=4)=[O:36])[CH:25]=[CH:24][CH:23]=3)[C:14]=12

Participants

3

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 66991126HCID 66991126, compound

Product 1

HCID 45380788HCID 45380788, compound

Procedure

To 3-(3-aminobenzyl)-1-benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molar equivalents of 3-(trifluoromethyl)phenyl isocyanate (Sigma-Aldrich) were added drop wise in ice-cold CH2Cl2. The reaction proceeded until completion as judged by TLC, was concentrated in vacuo, resuspended in 50:50 H20-CH3CN, and purified on a C18 column in CH3CN/H20/0.1% TFA (1-100% gradient) to yield final Cmpd BB6 1-(3-((4-amino-1-benzyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)methyl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea (ESI-MS m/z [M+H]+ found 518.4, calculated 518.2).

Workup

  1. concentrationwas concentrated in vacuo
  2. custompurified on a C18 column in CH3CN/H20/0.1% TFA (1-100% gradient)

Sources & evidence

ORD record
ord-e35d571939e24e0b902b94dd0d469beb
Source dataset
uspto-grants-2014_04
Patent number
US08697709B2

Reaction notes

Loading…