HCID 86761247, compound → HCID 57877635, compound

HRID 2266752Notes

Reaction equation

HRID 2266752 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[N:11]([C:12]([C:14]2[N:15]=[C:16]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH3:27])[CH:20]=3)[CH:18]=2)=[O:13])[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7]1)(=[O:3])[CH3:2]>[Pd].CO>[C:1]([O:4][CH2:5][C@H:6]1[CH2:7][NH:8][CH2:9][CH2:10][N:11]1[C:12]([C:14]1[N:15]=[C:16]([C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)[N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH3:27])[CH:20]=2)[CH:18]=1)=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86761247HCID 86761247, compound

Product 1

HCID 57877635HCID 57877635, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

((2R)-1-{[1-(3-Ethoxyphenyl)-2-(4-methylphenyl-1H-imidazol-4-yl]carbonyl}piperazin-2-yl)methyl acetate To 350 mg (0.330 mmol) of 10% palladium on carbon was added a solution of 3.55 g (5.95 mmol) of benzyl (3R)-3-[(acetyloxy)methyl]-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazine-1-carboxylate from Step C in 50 mL of anhydrous methanol. The resulting suspension was agitated under an atmosphere of hydrogen at 40 psi for 2 hours then filtered through a plug of Celite®. The plug was washed with methanol (75 mL), and the combined filtrates were concentrated in vacuo to yield the title compound as a colorless foam, which was used without further purification. 1H NMR (DMSO-d6): δ 7.85 (s, 1 H), 7.33 (t, J=8.2 Hz, 1 H), 7.21 (d, J=8.5 Hz, 2 H), 7.13 (d, J=8.5 Hz, 2 H), 6.98-7.00 (m, 1 H), 6.92 (s, 1 H), 6.77-6.79 (m, 1 H), 4.68-5.81 (m, 2 H), 4.18-4.59 (m, 3 H), 4.00 (q, J=6.8 Hz, 2 H), 2.72-3.02 (m, 4 H), 2.57-2.62 (m, 1 H), 2.27 (s, 3 H), 1.78-2.00 (m, 3 H), 1.27 (t, J=6.8 Hz, 3 H). LC/MS 463.5 (M+1).

Workup

  1. filtrationthen filtered through a plug of Celite®
  2. washThe plug was washed with methanol (75 mL)
  3. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-12ba58eb0c454d3e85d3513eda7b173d
Source dataset
uspto-grants-2010_12
Patent number
US07858629B2

Reaction notes

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