Water → 2-[4-(3,4-Dimethoxybenzene sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl ester

HRID 1392938Notes

Reaction equation

HRID 1392938 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([S:26](Cl)(=[O:28])=[O:27])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].C(N(CC)CC)C.O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:11][CH2:12][N:13]([S:26]([C:20]3[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=3)(=[O:28])=[O:27])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 22831866Methyl 2-(piperazin-1-yl)thiazole-5-carboxylate

Product 1

HCID 600321252-[4-(3,4-Dimethoxybenzene sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of intermediate 11 (200 mg, 0.886 mmol) in dichloromethane (7.5 mL) were added 3,4-dimethoxybenzenesulfonyl chloride (320 mg, 1.320 mmol) and triethylamine (220 mg, 2.169 mmol) under a N2 atmosphere. The reaction mixture was stirred at room temperature for 4 h. Water (10 mL) followed by dichloromethane (10 mL) were added to the reaction mixture and the organic layer was separated, dried on sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel to give the compound 12b as a solid (200 mg, 53.0%). HPLC: 99% (Rt 6.507 min).

Workup

  1. additionwere added to the reaction mixture
  2. customthe organic layer was separated
  3. customdried on sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c9ac763d8f624284831e3e9ee05db0f4
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

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