Hydrochloric Acid → HCID 71261264, compound

HRID 2411484Notes

Reaction equation

HRID 2411484 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].[F:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[O:40])=[CH:34][CH:33]=1.Cl>N1C=CC=CC=1>[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:39]([NH:38][C:35]2[CH:36]=[CH:37][C:32]([F:31])=[CH:33][CH:34]=2)=[O:40])=[O:16])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 709554-Fluorophenyl isocyanateHCID 86676778HCID 86676778, compound

Product 1

HCID 71261264HCID 71261264, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 pyridine (2 mL), 4-fluorophenyl isocyanate (64 mg) was added, and the mixture was stirred at room temperature. After completion of the reaction, to the reaction mixture was added dilute hydrochloric acid, 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 (89 mg).

Workup

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

Sources & evidence

ORD record
ord-8235b2d72e4a498084d728063defba60
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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