Methanol → 4-(6,7-Dimethoxy-9H-pyrimido[4,5-b]indol-4-yl)-piperazine-1-carbothioic acid [4-(pyrimidin-2-ylsulfamoyl)-phenyl]-amide

HRID 1465422Notes

Reaction equation

HRID 1465422 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]1[N:14]=[CH:15][N:16]=[C:17]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:6]2=1.N1C=CC=CC=1.[Cl-].[N:31]1[CH:36]=[CH:35][CH:34]=[N:33][C:32]=1[NH:37][S:38]([C:41]1[CH:46]=[CH:45][C:44]([NH:47][CH:48]=[S:49])=[CH:43][CH:42]=1)(=[O:40])=[O:39].CO>ClCCl>[N:31]1[CH:36]=[CH:35][CH:34]=[N:33][C:32]=1[NH:37][S:38]([C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:48]([N:21]2[CH2:20][CH2:19][N:18]([C:17]3[C:6]4[C:5]5[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=5)[NH:8][C:7]=4[N:14]=[CH:15][N:16]=3)[CH2:23][CH2:22]2)=[S:49])=[CH:43][CH:42]=1)(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 142937846,7-dimethoxy-4-piperazino-9H-pyrimido[4,5-b]indoleHCID 86601004N-Pyrimidin-2-yl-4-thioformylamino-benzenesulfonamide chloride

Product 1

HCID 113539534-(6,7-Dimethoxy-9H-pyrimido[4,5-b]indol-4-yl)-piperazine-1-carbothioic acid [4-(pyrimidin-2-ylsulfamoyl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6,7-dimethoxy-4-piperazino-9H-pyrimido[4,5-b]indole (200 mg, 0.64 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 and eluted with 5% methanol/dichloromethane and further recrystallized from dichloromethane/hexane to give 50 mg (16%).

Workup

  1. customto quench excess thiophosgene
  2. customthe residue after removal of solvent
  3. customwas purified by silica gel column chromatography
  4. washeluted with 5% methanol/dichloromethane
  5. customfurther recrystallized from dichloromethane/hexane
  6. customto give 50 mg (16%)

Sources & evidence

ORD record
ord-719fdc2a3d4140d3ad9e98c00f946bd0
Source dataset
uspto-grants-2015_04
Patent number
US08999988B2

Reaction notes

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