Water → HCID 71261265, compound

HRID 2411487Notes

Reaction equation

HRID 2411487 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][S:9]2(=[O:14])=[O:13])[CH:5]=[CH:4][C:3]=1[C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[CH3:30])[CH2:19][CH2:18]1)=[O:16].C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39].O>ClCCl>[CH3:30][C:24]1[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:23]=1[N:20]1[CH2:21][CH2:22][N:17]([C:15]([C:3]2[CH:4]=[CH:5][C:6]([N:8]3[CH2:12][CH2:11][CH2:10][S:9]3(=[O:14])=[O:13])=[CH:7][C:2]=2[NH:1][C:38](=[O:40])[CH3:39])=[O:16])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86676778HCID 86676778, compound

Product 1

HCID 71261265HCID 71261265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-Amino-4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (100 mg) described in Example 103 was dissolved in dichloromethane (2 mL), triethylamine (0.07 mL) and acetyl chloride (0.03 mL) were added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (24 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-543e83ca43b14fecb0c4d713649da03d
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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