3-(Trifluoromethyl)phenyl isocyanate → 1-[2-(6,7-Dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]-3-(3-trifluoromethylphenyl)urea

HRID 2108917Notes

Reaction equation

HRID 2108917 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[N:22]=[CH:21][N:20]=[C:19]2[NH:28][C:29]1[S:30][C:31]2[CH:37]=[C:36]([NH2:38])[CH:35]=[CH:34][C:32]=2[N:33]=1>O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[N:22]=[CH:21][N:20]=[C:19]2[NH:28][C:29]1[S:30][C:31]2[CH:37]=[C:36]([NH:38][C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=3)=[O:11])[CH:35]=[CH:34][C:32]=2[N:33]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 86248039N2-(6,7-dimethoxyquinazolin-4-yl)benzothiazole-2,6-diamine

Product 1

HCID 231325061-[2-(6,7-Dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]-3-(3-trifluoromethylphenyl)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[2-(6,7-Dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]-3-(3-trifluoromethylphenyl)urea was prepared from 3-trifluoromethylphenyl isocyanate (16 μL, 0.113 mmol) and N2-(6,7-dimethoxyquinazolin-4-yl)benzothiazole-2,6-diamine (40 mg, 0.113 mmol) according to GP 3. The mixture was poured into water (20 mL) and the resulting precipitate was purified by pTLC (dichloromethane:methanol=9:1) to obtain a yellow solid (44 mg, 81 μmol, 72%). LC/ESI-MS: m/z=541 [M+H]+; m/z=539 [M−H]−; Rt=3.59 min.

Workup

  1. customthe resulting precipitate was purified by pTLC (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-fc3736fa68934ccba4962c352bd18bd7
Source dataset
uspto-grants-2009_04
Patent number
US07514460B2

Reaction notes

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