1-Methylpiperazine → HCID 22250086, compound

HRID 889899Notes

Reaction equation

HRID 889899 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][C:13]([C:17](Cl)=[O:18])=[C:14]([CH3:16])[N:15]=3)[S:10][C:3]=12.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][C:13]([C:17]([N:24]4[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]4)=[O:18])=[C:14]([CH3:16])[N:15]=3)[S:10][C:3]=12

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 22250084HCID 22250084, compound

Product 1

HCID 22250086HCID 22250086, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carbonyl chloride, (0.28 g, 0.85 mmol), dry dichloromethane (1.5 mL), and 1-methylpiperazine (0.21 mL, 1.87 mmol) was stirred at room temperature for four hours. A gas discharge and immediate solution were noted. The reaction mixture was evaporated directly onto silica gel and purified through silica gel chromatography to afford [2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazol-5-yl]-(4-methyl-piperazin-1-yl)-methanone (0.234 g) in 70% yield. C17H17ClN4OS2: APCI 393.2/395.2 (pos.); 1H NMR (d6-DMSO): δ 8.68 (d, 1H, J=5.4 Hz), 8.32 (s, 1H), 7.64 (d, 1H, J=5.4 Hz), 3.6–3.4 (bm, 4H), 2.38 (s, 3H), 2.4–2.2 (bm, 4H), 2.17 (s, 3H) ppm.

Workup

  1. customThe reaction mixture was evaporated directly onto silica gel
  2. custompurified through silica gel chromatography

Sources & evidence

ORD record
ord-114577f36e3b40609c07eaf1d0e42ef3
Source dataset
uspto-grants-2006_02
Patent number
US06995171B2

Reaction notes

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