2-[2-[Isobutyl-(4-trifluoromethyl-phenyl)-amino]-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pent-4-enoic acid methyl ester → 2-[2-[Isobutyl-(4-trifluoromethyl-phenyl)-amino]-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pentanoic acid methyl ester

HRID 2427887Notes

Reaction equation

HRID 2427887 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH:4]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[N:12]=[C:11]([N:25]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[CH:10]=1)[CH2:5][C:6]([CH3:8])=[CH2:7]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:40])[CH:4]([C:9]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:20]=2)[N:12]=[C:11]([N:25]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=2)[CH:10]=1)[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 1

HCID 591617302-[2-[Isobutyl-(4-trifluoromethyl-phenyl)-amino]-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pent-4-enoic acid methyl ester

Product 1

HCID 591617342-[2-[Isobutyl-(4-trifluoromethyl-phenyl)-amino]-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pentanoic acid methyl esterYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-[2-[isobutyl-(4-trifluoromethyl-phenyl)-amino]-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pent-4-enoic acid methyl ester (40 mg, 0.07 mmol), Pd/C (10%, 5 mg) in methanol (10 mL) was hydrogenated for 4 h. The mixture was filtered through Celite, washed with methanol, evaporated. The residue was dissolved in CH2Cl2, filtered and evaporated to give the product as colorless oil (40 mg, 100%). 1H NMR (300 MHz, CDCl3) δ 8.12 (d, J=8.29 Hz, 2H), 7.70 (d, J=8.29 Hz, 2H), 7.64 (d, J=8.67 Hz, 2H), 7.38 (d, J=8.67 Hz, 2H), 7.18 (s, 1H), 6.57 (s, 1H), 3.96 (d, J=7.16 Hz, 2H), 3.66 (s, 3H), 2.10-2.23 (m, 1H), 1.90 (dt, J=7.72, 13.56 Hz, 1H), 1.62 (dt, J=6.92, 13.66 Hz, 1H), 1.40-1.52 (m, 1H), 0.97 (d, J=6.78 Hz, 6H), 0.89 (dd, J=4.33, 6.59 Hz, 5H). MS m/e 567.3 (M+H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with methanol
  3. customevaporated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4aead984026b4ac99dd513f6563629aa
Source dataset
uspto-grants-2011_06
Patent number
US07968725B2

Reaction notes

Loading…