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

HRID 1392942
Notes
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Reaction equation

HRID 1392942 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][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.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:23]([C:20]3[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=3)(=[O:25])=[O:24])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22831866Methyl 2-(piperazin-1-yl)thiazole-5-carboxylate

Product 1

HCID 691978862-[4-(Toluene-4-sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of compound 11 (200 mg, 0.886 mmol) in dichloromethane (7.5 mL) were added 4-methyl benzenesulfonyl chloride (251 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 12e as a solid (275 mg, 82%). HPLC: 99.62% (Rt=9.22 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-bd1fd42a549349d18a63c763720c6b7a
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07345043B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes