Methanol → 4-(9-Thia-1,5,7-triaza-fluoren-8-yl)-piperazine-1-carbothioic acid [4-(Pyrimidin-2-ylsulfamoyl)-phenyl]-amide

HRID 2052846Notes

Reaction equation

HRID 2052846 reaction equation
[N:1]1([C:7]2[C:8]3[S:15][C:14]4[N:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl-].[N:27]1[CH:32]=[CH:31][CH:30]=[N:29][C:28]=1[NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([NH:43][CH:44]=[S:45])=[CH:39][CH:38]=1)(=[O:36])=[O:35].CO>ClCCl>[N:27]1[CH:32]=[CH:31][CH:30]=[N:29][C:28]=1[NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[N:12]=[CH:11][N:10]=[C:9]4[C:8]=3[S:15][C:14]3[N:16]=[CH:17][CH:18]=[CH:19][C:13]4=3)[CH2:6][CH2:5]2)=[S:45])=[CH:39][CH:38]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 673902864-Piperazinopyrido[3',2';4,5]thieno[3,2-d]pyrimidineHCID 86601004N-Pyrimidin-2-yl-4-thioformylamino-benzenesulfonamide chloride

Product 1

HCID 590205024-(9-Thia-1,5,7-triaza-fluoren-8-yl)-piperazine-1-carbothioic acid [4-(Pyrimidin-2-ylsulfamoyl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-piperazinopyrido[3′,2′;4,5]thieno[3,2-d]pyrimidine (200 mg, 0.74 mmol) and pyridine (0.5 mL, 7.9 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 60 mg (15%).

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 60 mg (15%)

Sources & evidence

ORD record
ord-79b7308711f64f608b638a44c50dd5c2
Source dataset
uspto-grants-2008_02
Patent number
US07326713B2

Reaction notes

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