3-(Trifluoromethyl)phenyl isocyanate → HCID 178522215, compound

HRID 2409107Notes

Reaction equation

HRID 2409107 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[NH:20][N:19]=[C:18]([CH:21]4[CH2:23][CH2:22]4)[CH:17]=3)[CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1>C(Cl)Cl>[CH:21]1([C:18]2[CH:17]=[C:16]([NH:15][C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:33]([NH:32][C:28]5[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:24])([F:35])[F:36])[CH:27]=5)=[O:34])=[CH:3][CH:4]=4)[N:14]=3)[NH:20][N:19]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 178507724HCID 178507724, compound

Product 1

HCID 178522215HCID 178522215, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N2-(4-aminophenyl)-N4-(3-cyclopropyl-1H-pyrazol-5-yl)pyrimidine-2,4-diamine (0.022 g, 0.07 mmol) in CH2Cl2 (10 mL) was cooled in an ice-water bath. To this 3-(trifluoromethyl)phenyl isocyanate (0.030 mL, 0.2 mmol) diluted in CH2Cl2 (5 mL) was added drop wise. The reaction was allowed to warm to room temperature and left stirring for 1 hour. The reaction proceeded until completion as judged by TLC and LC-MS. The reaction mixture 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 AD75. ESI-MS m/z[M+H]+. Found 495.5. Calculated 495.2.

Workup

  1. additionwas added drop wise
  2. waitleft
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified on a C18 column in CH3CN/H2O/0.1% TFA (1-100% gradient)
  5. customto afford AD75

Sources & evidence

ORD record
ord-78798effce894f6180766250db2c1c59
Source dataset
uspto-grants-2014_08
Patent number
US08815885B2

Reaction notes

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