Water → 4-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl-thiazole-5-carboxylic acid methyl ester

HRID 1392952Notes

Reaction equation

HRID 1392952 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][N:17]([CH3:32])[C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[C:23]2[S:28](Cl)(=[O:30])=[O:29].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:28]([C:23]3[C:24]4[C:19](=[C:18]([N:17]([CH3:32])[CH3:16])[CH:27]=[CH:26][CH:25]=4)[CH:20]=[CH:21][CH:22]=3)(=[O:30])=[O:29])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 22831866Methyl 2-(piperazin-1-yl)thiazole-5-carboxylate

Product 1

HCID 691997234-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl-thiazole-5-carboxylic acid methyl esterYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 11 (200 mg, 0.886 mmol) in dichloromethane (7.5 mL) were added 5-dimethylamino-naphthalene-1-sulfonyl chloride (356 mg, 1.320 mmol) and triethylamine (220 mg, 2.169 mmol) under 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 sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel to give the compound 12k as a solid (233 mg, 57.50%). HPLC: 99.04% (Rt=12.33 min).

Workup

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

Sources & evidence

ORD record
ord-57c60e8e0d7e41729601ec3fe0b50540
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

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