Citric Acid → HCID 178456919, compound

HRID 1620685Notes

Reaction equation

HRID 1620685 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20][C:21]#[CH:22])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:8][CH2:7]1.[C:33]([OH:45])(=[O:44])[CH2:34][C:35]([CH2:40][C:41]([OH:43])=[O:42])([C:37]([OH:39])=[O:38])[OH:36]>C(O)C>[C:33]([OH:45])(=[O:44])[CH2:34][C:35]([CH2:40][C:41]([OH:43])=[O:42])([C:37]([OH:39])=[O:38])[OH:36].[F:32][C:2]([F:1])([F:31])[C:3]1[CH:26]=[C:25]([C:27]([F:29])([F:30])[F:28])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20][C:21]#[CH:22])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 311Citric AcidHCID 178456914HCID 178456914, compound

Product 1

HCID 178456919HCID 178456919, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (1 g) in ethanol (15 mL) was added citric acid (0.40 g). The reaction mixture was stirred at 80° C. for 20 min, the solvent was evaporated under reduced pressure, and the residue was recrystallized from 2-propanol/heptane to give the title compound (1.21 g).

Workup

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

Sources & evidence

ORD record
ord-88c9bf5d2f554543b3f89ff385f42f22
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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