3-(Trifluoromethyl)phenyl isocyanate → HCID 45381212, compound

HRID 2365764Notes

Reaction equation

HRID 2365764 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@H:18]3[CH2:22][CH2:21][O:20][CH2:19]3)[N:9]=2)=[CH:4][CH:3]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1>C(Cl)Cl>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([C@H:18]3[CH2:22][CH2:21][O:20][CH2:19]3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:32]([NH:31][C:27]4[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=4)=[O:33])=[CH:3][CH:4]=3)[C:16]=12

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 58506741HCID 58506741, compound

Product 1

HCID 45381212HCID 45381212, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(4-aminophenyl)-1-((S)-tetrahydrofuran-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.1 g, 0.34 mmol) in CH2Cl2 (10 mL) was cooled in an ice-water bath. To this, 3-(trifluoromethyl)phenyl isocyanate (0.047 mL, 0.34 mmol) diluted in CH2Cl2 (5 mL) was added dropwise. The reaction was allowed to warm to room temperature and left stirring for 12 hours. Reaction completion was judged by TLC and LC-MS. The reaction mixture was filtered, dried onto silica, and purified using silica gel column chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient) to afford final compound AD66. ESI-MS m/z [M+H]+ found 484.4, calculated 484.2.

Workup

  1. additionwas added dropwise
  2. waitleft
  3. customReaction completion
  4. filtrationThe reaction mixture was filtered
  5. customdried onto silica
  6. custompurified

Sources & evidence

ORD record
ord-3302bdbcce494fa78b27837ca648de03
Source dataset
uspto-grants-2014_04
Patent number
US08697709B2

Reaction notes

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