N2-{[({3-(4-Chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetyl)amino][2-(trifluoromethyl)phenyl]acetyl}-2-methylalaninamide → N2-{({[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}amino) [2-(trifluoromethyl)phenyl]acetyl}-2-methylalaninamide

HRID 574159Notes

Reaction equation

HRID 574159 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](/[CH:13]=[CH:14]/[C:15]([F:18])([F:17])[F:16])[C:11](=[O:19])[N:10]([CH2:20][C:21]([NH:23][CH:24]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]([F:43])([F:42])[F:41])[C:25]([NH:27][C:28]([CH3:33])([C:30]([NH2:32])=[O:31])[CH3:29])=[O:26])=[O:22])[N:9]=2)=[CH:4][CH:3]=1>CO.[Pt]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C:15]([F:16])([F:17])[F:18])[C:11](=[O:19])[N:10]([CH2:20][C:21]([NH:23][CH:24]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]([F:41])([F:42])[F:43])[C:25]([NH:27][C:28]([CH3:29])([C:30]([NH2:32])=[O:31])[CH3:33])=[O:26])=[O:22])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 56932706N2-{[({3-(4-Chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetyl)amino][2-(trifluoromethyl)phenyl]acetyl}-2-methylalaninamide

Product 1

HCID 87160584N2-{({[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}amino) [2-(trifluoromethyl)phenyl]acetyl}-2-methylalaninamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of 25 mg (39 μmol) of the compound of Example 31 in 10 ml of methanol was hydrogenated in an H-Cube fitted with a platinum cartridge (5% Pt/C) (continuous-flow hydrogenation apparatus from Thales Nano, Budapest, Model HC-2-SS) at a flow rate of 1 ml/min, at 60° C. and under hydrogen at standard pressure. The resulting solution was freed from methanol on a rotary evaporator, and the residue was dissolved in 2 ml of acetonitrile and purified by preparative HPLC [Method 7]. This gave 8 mg (32% of theory) of the title compound.

Workup

  1. customThe resulting solution was freed from methanol on a rotary evaporator
  2. dissolutionthe residue was dissolved in 2 ml of acetonitrile
  3. custompurified by preparative HPLC [Method 7]

Sources & evidence

ORD record
ord-3d537ae618694a4088334381873e4a78
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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