Water → HCID 69238095, compound

HRID 1392950Notes

Reaction equation

HRID 1392950 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].[C:16]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=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:22]([C:19]3[CH:18]=[CH:17][C:16]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)(=[O:24])=[O:23])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 22831866Methyl 2-(piperazin-1-yl)thiazole-5-carboxylate

Product 1

HCID 69238095HCID 69238095, compoundYield 51.2%

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 4-biphenyl sulfonyl chloride (333 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 12j as a solid (200 mg, 51.2%). HPLC: 99.88% (Rt=15.46 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-e9b531accfce44ad8e1e01f96ce6d6a2
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

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