3-(Trifluoromethyl)phenyl isocyanate → HCID 45380892, compound

HRID 2365778Notes

Reaction equation

HRID 2365778 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:18]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)[C:3]=12.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:33]=[C:34]([N:38]=[C:39]=[O:40])[CH:35]=[CH:36][CH:37]=1>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:18]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:39]([NH:38][C:34]4[CH:35]=[CH:36][CH:37]=[C:32]([C:31]([F:30])([F:41])[F:42])[CH:33]=4)=[O:40])=[CH:13][CH:12]=3)[C:3]=12

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 58506753HCID 58506753, compound

Product 1

HCID 45380892HCID 45380892, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-tert-butyl 3-(4-amino-3-(4-aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidine-1-carboxylate (0.035 g, 0.09 mmol) in CH2Cl2 (10 mL) was cooled in an ice-water bath. To this, 3-(trifluoromethyl)phenyl isocyanate (0.012 mL, 0.09 mmol) diluted in CH2Cl2 (5 mL) was added dropwise. The reaction was allowed to warm to room temperature and left stirring for 6 hours. The reaction proceeded until completion as judged by TLC and LC-MS, was concentrated in vacuo, resuspended in 50:50 H2O—CH3CN, and purified on a C18 column in CH3CN/H2O/0.1% TFA (1-100% gradient) to afford AD78. ESI-MS m/z [M+H]+ found 583.5, calculated 583.2.

Workup

  1. additionwas added dropwise
  2. waitleft
  3. concentrationwas concentrated in vacuo
  4. custompurified on a C18 column in CH3CN/H2O/0.1% TFA (1-100% gradient)
  5. customto afford AD78

Sources & evidence

ORD record
ord-bdbda4b1016d4b998ffd99a3b3022452
Source dataset
uspto-grants-2014_04
Patent number
US08697709B2

Reaction notes

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