Acetone → HCID 59846291, compound

HRID 1697076Notes

Reaction equation

HRID 1697076 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:27])/[CH:9]=[CH:10]/[C:11]2[CH:26]=[CH:25][C:14]([C:15]([NH:17][CH:18]3[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]3)=[O:16])=[CH:13][CH:12]=2)=[C:4]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:3]=1.C1COCC1.CC(C)=O>CCO.[Pt+3]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:27])[CH2:9][CH2:10][C:11]2[CH:26]=[CH:25][C:14]([C:15]([NH:17][CH:18]3[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]3)=[O:16])=[CH:13][CH:12]=2)=[C:4]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 59846223HCID 59846223, compound

Product 1

HCID 59846291HCID 59846291, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178527101HCID 178527101, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-N-(4-hydroxy-cyclohexyl)-benzamide (197 mg) and platinum (V) oxide (50 mg) in a mixture of EtOH, THF and acetone (100/50/100 mL) was stirred under H2 (balloon pressure) at RT for 1 h. The resulting mixture was filtered, and the filtrate concentrate under reduced pressure to yield 4-[3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propyl]-N-(4-hydroxy-cyclohexyl)-benzamide (190 mg).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate concentrate under reduced pressure

Sources & evidence

ORD record
ord-798ac5af0975438ea67a67b57e487acd
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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