Methanol → 4-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carbothioic acid [4-(pyrimidin-2-ylsulfamoyl)-phenyl]-amide

HRID 970452Notes

Reaction equation

HRID 970452 reaction equation
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl-].[N:28]1[CH:33]=[CH:32][CH:31]=[N:30][C:29]=1[NH:34][S:35]([C:38]1[CH:43]=[CH:42][C:41]([NH:44][CH:45]=[S:46])=[CH:40][CH:39]=1)(=[O:37])=[O:36].CO>ClCCl>[N:28]1[CH:33]=[CH:32][CH:31]=[N:30][C:29]=1[NH:34][S:35]([C:38]1[CH:43]=[CH:42][C:41]([NH:44][C:45]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[C:16]4[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=4)[N:10]=[CH:9][N:8]=3)[CH2:2][CH2:3]2)=[S:46])=[CH:40][CH:39]=1)(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 27584846,7-Dimethoxy-4-piperazin-1-yl-quinazolineHCID 86601004N-Pyrimidin-2-yl-4-thioformylamino-benzenesulfonamide chloride

Product 1

HCID 590205174-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carbothioic acid [4-(pyrimidin-2-ylsulfamoyl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(1-piperazinyl)-6,7-dimethoxy quinazoline (200 mg, 0.73 mmol) and pyridine (0.5 mL, 6.4 mmol) in dichloromethane (20 mL) was added a solution of product 1d in dichloromethane (20 mL) and stirred overnight. Methanol was added for quenching excess thiophosgene, and the residue after removal of solvent was purified by silica gel column chromatography eluting with 5% methanol/dichloromethane and further recrystallized from dichloromethane/hexane to give 80 mg (20%).

Workup

  1. customfor quenching excess thiophosgene
  2. customthe residue after removal of solvent
  3. customwas purified by silica gel column chromatography
  4. washeluting with 5% methanol/dichloromethane
  5. customfurther recrystallized from dichloromethane/hexane
  6. customto give 80 mg (20%)

Sources & evidence

ORD record
ord-d069e949f8244173a55632312eceb130
Source dataset
uspto-grants-2007_12
Patent number
US07312226B2

Reaction notes

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