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

HRID 1038967Notes

Reaction equation

HRID 1038967 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 this was stirred overnight. Methanol was added to quench 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. customto quench 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-98794221adc34f9e9c6af61142094bb4
Source dataset
uspto-grants-2013_10
Patent number
US08552018B2

Reaction notes

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