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

HRID 1465417Notes

Reaction equation

HRID 1465417 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 the mixture 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 was 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. washeluting with 5% methanol/dichloromethane
  5. customwas further recrystallized from dichloromethane/hexane
  6. customto give 50 mg (16%)

Sources & evidence

ORD record
ord-731349550bb14d4eb25596bc91c384b3
Source dataset
uspto-grants-2015_04
Patent number
US08999988B2

Reaction notes

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