HCID 178439237, compound → HCID 178471774, compound

HRID 505305Notes

Reaction equation

HRID 505305 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([N:26]([CH2:29][C@H:30]4[CH2:35][CH2:34][C@H:33]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:32][CH2:31]4)[CH2:27][CH3:28])=[CH:24][CH:23]=[C:22]([C:42]([CH3:44])=[CH2:43])[N:21]=3)[C@H:14]2[CH3:45])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>[Pd].CCOC(C)=O>[F:46][C:2]([F:1])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([N:26]([CH2:29][C@H:30]4[CH2:35][CH2:34][C@H:33]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:32][CH2:31]4)[CH2:27][CH3:28])=[CH:24][CH:23]=[C:22]([CH:42]([CH3:44])[CH3:43])[N:21]=3)[C@H:14]2[CH3:45])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 1

HCID 178439237HCID 178439237, compound

Product 1

HCID 178471774HCID 178471774, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 10% palladium on carbon (2.0 mg) in a solution of ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-isopropenylpyridin-3-yl](ethyl)amino]methyl}cyclohexyl)acetate (19.0 mg, 0.0284 mmol) in EtOAc (5 mL) was stirred under H2 (double balloon pressure) for 4 h. The reaction mixture was filtered through a plug of Celite and the filtrate was concentrated in vacuo to afford ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-isopropylpyridin-3-yl](ethyl)amino]methyl}cyclohexyl)acetate as a colorless oil. LCMS calc.=672.3; found=672.3 (M+1)+. 1H NMR (600 MHz, CDCl3): δ 7.87 (s, 1 H); 7.78 (s, 2 H); 7.36 (d, J=7.6 Hz, 1 H); 7.03 (d, J=7.8 Hz, 1 H); 5.77 (d, J=8.2 Hz, 1 H); 4.95 (d, J=16.6 Hz, 1 H); 4.41-4.35 (m, 2 H); 4.08 (q, J—7.1 Hz, 2 H); 3.01 (s, 1 H); 2.90 (s, 2 H); 2.79-2.71 (m, 2 H); 2.12 (d, J=6.5 Hz, 2 H); 1.84-1.65 (m, 5H); 1.30-1.20 (m, 10 H); 0.98-0.86 (m, 7 H); 0.71 (d, J=6.3 Hz, 3 H).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3dc05a17020449498a7da3768619ccc3
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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