Maleic Acid → HCID 178456913, compound

HRID 1620574Notes

Reaction equation

HRID 1620574 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][CH:8](/[CH:11]=[C:12]2/[C:13]([NH:18][CH2:19][C:20]#[CH:21])=[N:14][C:15](=[O:17])[S:16]/2)[CH2:7]1.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]>C(O)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36].[F:31][C:2]([F:1])([F:30])[C:3]1[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[CH:22][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][CH:8](/[CH:11]=[C:12]2/[C:13]([NH:18][CH2:19][C:20]#[CH:21])=[N:14][C:15](=[O:17])[S:16]/2)[CH2:7]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 178456912HCID 178456912, compound

Product 1

HCID 178456913HCID 178456913, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]pyrrolidin-3-yl}methylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (740 mg) in ethanol (10 mL) was added maleic acid (186 mg). The reaction mixture was stirred at 80° C. for 20 min, the solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol/heptane to give the title compound (800 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was recrystallized from ethanol/heptane

Sources & evidence

ORD record
ord-02165552704e4c10a4aaf47f1ccd6814
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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