Methanol → 4-(6,7-Dimethoxy-9H-1,3,9-triaza-fluoren-4-yl)-piperazine-1-carbothioic acid(benzo[1,3]dioxol-5-ylmethyl)-amide

HRID 970457Notes

Reaction equation

HRID 970457 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-].[O:31]1[C:35]2[CH:36]=[CH:37][C:38]([CH2:40][NH:41][CH:42]=[S:43])=[CH:39][C:34]=2[O:33][CH2:32]1.CO>ClCCl>[O:31]1[C:35]2[CH:36]=[CH:37][C:38]([CH2:40][NH:41][C:42]([N:21]3[CH2:20][CH2:19][N:18]([C:17]4[C:6]5[C:5]6[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=6)[NH:8][C:7]=5[N:14]=[CH:15][N:16]=4)[CH2:23][CH2:22]3)=[S:43])=[CH:39][C:34]=2[O:33][CH2:32]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 142937846,7-dimethoxy-4-piperazino-9H-pyrimido[4,5-b]indoleHCID 86601006N-Benzo[1,3]dioxol-5-ylmethyl-thioformamide chloride

Product 1

HCID 112374894-(6,7-Dimethoxy-9H-1,3,9-triaza-fluoren-4-yl)-piperazine-1-carbothioic acid(benzo[1,3]dioxol-5-ylmethyl)-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 the solution of product 1c 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 further recrystallized from dichloromethane/hexane to give 130 mg (40%).

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 130 mg (40%)

Sources & evidence

ORD record
ord-b9255261fed345d893258271cb08debc
Source dataset
uspto-grants-2007_12
Patent number
US07312226B2

Reaction notes

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