Water → 4-[(3-Bromophenyl)amino]-6-[(4-{N-[(tert-butyloxycarbonyl)methyl]-N-[2-(acetylsulphanyl)ethyl]amino)-1-oxo-2-buten-1-yl)-amino]-7-methoxy-quinazoline

HRID 488421Notes

Reaction equation

HRID 488421 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:46][CH3:47])=[C:21]([NH:24][C:25](=[O:45])[CH:26]=[CH:27][CH2:28][N:29]([CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:30][CH2:31]OS(C)(=O)=O)[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1.O>CN(C)C=O>[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:46][CH3:47])=[C:21]([NH:24][C:25](=[O:45])[CH:26]=[CH:27][CH2:28][N:29]([CH2:37][C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[CH2:30][CH2:31][S:3][C:1](=[O:4])[CH3:2])[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23670855Potassium ethanethioateHCID 572144434-[(3-bromophenyl)amino]-6-[(4-(N-[(tert-butyloxycarbonyl)methyl]-N-[2-(methylsulphonyloxy)ethyl]amino}-1-oxo-2-buten-1-yl)amino]-7-methoxy-quinazoline

Product 1

HCID 738794514-[(3-Bromophenyl)amino]-6-[(4-{N-[(tert-butyloxycarbonyl)methyl]-N-[2-(acetylsulphanyl)ethyl]amino)-1-oxo-2-buten-1-yl)-amino]-7-methoxy-quinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

34 mg of potassium thioacetate are added to 150 mg of 4-[(3-bromophenyl)amino]-6-[(4-(N-[(tert-butyloxycarbonyl)methyl]-N-[2-(methylsulphonyloxy)ethyl]amino}-1-oxo-2-buten-1-yl)amino]-7-methoxy-quinazoline in 1 ml of dimethylformamide at ambient temperature. The reaction mixture is stirred overnight at ambient temperature and then combined with water for working up. The aqueous phase is separated off and extracted with ethyl acetate, the combined organic phases are dried over magnesium sulphate and freed from solvent in the rotary evaporator. Yield: 20 mg (14% of theory), Rf value: 0.62 (silica gel, ethyl acetate/methanol=15:1) Mass spectrum (EI): m/z=643, 645 [M]+

Workup

  1. customThe aqueous phase is separated off
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined organic phases are dried over magnesium sulphate
  4. customfreed from solvent in the rotary evaporator

Sources & evidence

ORD record
ord-96fe93f0c8294e8a818701511fb4c946
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

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