3-Methoxyphenyl isocyanate → 1-[2-(6,7-Dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]-3-(3-methoxyphenyl)urea

HRID 2108915Notes

Reaction equation

HRID 2108915 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]2[NH:26][C:27]1[S:28][C:29]2[CH:35]=[C:34]([NH2:36])[CH:33]=[CH:32][C:30]=2[N:31]=1>O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]2[NH:26][C:27]1[S:28][C:29]2[CH:35]=[C:34]([NH:36][C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:11])[CH:33]=[CH:32][C:30]=2[N:31]=1

Participants

4

Reactant 2

HCID 878433-Methoxyphenyl isocyanateHCID 86248039N2-(6,7-dimethoxyquinazolin-4-yl)benzothiazole-2,6-diamine

Product 1

HCID 116847841-[2-(6,7-Dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]-3-(3-methoxyphenyl)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[2-(6,7-Dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]-3-(3-methoxyphenyl)urea was prepared from 3-methoxyphenyl isocyanate (15 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 (26 mg, 53 μmol, 46%). LC/ESI-MS: m/z=503 [M+H]+; m/z=501 [M−H]−; Rt=3.12 min.

Workup

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

Sources & evidence

ORD record
ord-86b4347ac6fc43fb9f29150963bf8208
Source dataset
uspto-grants-2009_04
Patent number
US07514460B2

Reaction notes

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