Triethylamine → HCID 86607109, compound

HRID 900887Notes

Reaction equation

HRID 900887 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([NH:11][C:12]1[S:13][C:14]([S:18](Cl)(=[O:20])=[O:19])=[C:15]([CH3:17])[N:16]=1)(=[O:10])[CH3:9].C([N:24](CC)CC)C>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([NH:24][S:18]([C:14]2[S:13][C:12]([NH:11][C:8](=[O:10])[CH3:9])=[N:16][C:15]=2[CH3:17])(=[O:20])=[O:19])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chloride

Product 1

HCID 86607109HCID 86607109, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-methylpiperazine (1.18 g, 11.8 mmol) in THF (24 ml) was added at 0° C. (ice water bath) commercially available 2-acetamido-4-methylthiazole-5-sulfonyl chloride (2.0 g, 7.85 mmol) and triethylamine (1.2 ml, 8.6 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH 9:1) and subsequent crystallization (dichloromethane/MeOH/hexane) to yield 2-acetamido-4-methyl-thiazole-5-sulfonic acid (4-methylpiperazinyl)-amide (1.85 g, 74%) as a white solid. MS (ISP) 319.0 [(M+H)+]; mp 245° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH 9:1) and subsequent crystallization (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record
ord-5acdeb9ba7e6475eb170547a287ef355
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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