HCID 10204107, compound → HCID 10136447, compound

HRID 1830995Notes

Reaction equation

HRID 1830995 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]\[CH3:23])=[C:17]([C:24]([F:27])([F:26])[F:25])[CH:16]=2)=[O:13])=[CH:4][CH:3]=1.[H][H]>CO.[Pt]>[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH3:23])=[C:17]([C:24]([F:25])([F:26])[F:27])[CH:16]=2)=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10204107HCID 10204107, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10136447HCID 10136447, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-[4-pyridinylmethyl]amino-N-[4-[(Z)-1-propenyl]-3-(trifluoromethyl)phenyl]benzamide (Example 8; 0.80 g, 1.75 mmol) in methanol (25 mL) is hydrogenated at atmospheric pressure over 5% platinum on carbon (0.2 g) at 22° C. The calculated amount of hydrogen is taken up after 12 hours. The mixture is then filtered and the solvent is evaporated under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 20% dichloromethane in EtOAc and recrystallised from diethylether-hexane to give the title compound as a colourless crystalline solid; m.p. 134–135° C.

Workup

  1. filtrationThe mixture is then filtered
  2. customthe solvent is evaporated under reduced pressure
  3. customto yield the crude product which
  4. customis purified by column chromatography on silica gel, eluent 20% dichloromethane in EtOAc
  5. customrecrystallised from diethylether-hexane

Sources & evidence

ORD record
ord-fb195787d20f4a8aac6f3c0a68d4db68
Source dataset
uspto-grants-2006_06
Patent number
US07067543B2

Reaction notes

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