Fumaric Acid → HCID 178456918, compound

HRID 1620481Notes

Reaction equation

HRID 1620481 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:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>C(O)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[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 444972Fumaric AcidHCID 178456914HCID 178456914, compound

Product 1

HCID 178456918HCID 178456918, compoundYield 57.2%

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 (9.95 g) in ethanol (100 mL) was added fumaric acid (2.43 g). The 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 (7.08 g).

Workup

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

Sources & evidence

ORD record
ord-a4ffa91683044d59bf66e49a4b75669b
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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