Methanol → 4-(9-Thia-1,5,7-triaza-fluoren-8-yl)-piperazine-1-carbothioic acid (benzo[1,3]dioxol-5-ylmethyl)-amide

HRID 2052832Notes

Reaction equation

HRID 2052832 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-].[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([CH2:36][NH:37][CH:38]=[S:39])=[CH:35][C:30]=2[O:29][CH2:28]1.CO>ClCCl>[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([CH2:36][NH:37][C:38]([N:4]3[CH2:3][CH2:2][N:1]([C:7]4[N:12]=[CH:11][N:10]=[C:9]5[C:8]=4[S:15][C:14]4[N:16]=[CH:17][CH:18]=[CH:19][C:13]5=4)[CH2:6][CH2:5]3)=[S:39])=[CH:35][C:30]=2[O:29][CH2:28]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 673902864-Piperazinopyrido[3',2';4,5]thieno[3,2-d]pyrimidineHCID 86601006N-Benzo[1,3]dioxol-5-ylmethyl-thioformamide chloride

Product 1

HCID 114198954-(9-Thia-1,5,7-triaza-fluoren-8-yl)-piperazine-1-carbothioic acid (benzo[1,3]dioxol-5-ylmethyl)-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 1c 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 110 mg (32%).

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 110 mg (32%)

Sources & evidence

ORD record
ord-66c4d5f152c34719bcbabe719f889a04
Source dataset
uspto-grants-2008_02
Patent number
US07326712B2

Reaction notes

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