HCID 66775543, compound → HCID 66775371, compound

HRID 1645194Notes

Reaction equation

HRID 1645194 reaction equation
[F:1][C:2]([F:39])([F:38])[O:3][C:4]1[CH:5]=[C:6]([CH:35]=[CH:36][CH:37]=1)[CH2:7][N:8]([CH2:17][CH:18]1[CH:23]2[CH:19]1[CH2:20][N:21]([CH2:24][C:25]([O:27]CC1C=CC=CC=1)=[O:26])[CH2:22]2)[C:9]([C:11]1[N:12]=[CH:13][N:14]([CH3:16])[CH:15]=1)=[O:10]>CO.[OH-].[OH-].[Pd+2]>[F:39][C:2]([F:1])([F:38])[O:3][C:4]1[CH:5]=[C:6]([CH:35]=[CH:36][CH:37]=1)[CH2:7][N:8]([CH2:17][CH:18]1[CH:19]2[CH:23]1[CH2:22][N:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20]2)[C:9]([C:11]1[N:12]=[CH:13][N:14]([CH3:16])[CH:15]=1)=[O:10]

Participants

4

Reactant 1

HCID 66775543HCID 66775543, compound

Product 1

HCID 66775371HCID 66775371, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a par bottle charged with benzyl 2-(6-((N-(3-(trifluoromethoxy)benzyl)-1-methyl-1H-imidazole-4-carboxamido)methyl)-3-aza-bicyclo[3.1.0]hexan-3-yl)acetate (2.7 gm, 5.07 mmol) in 80 mL CH3OH, was added 300 mg palladium hydroxide on carbon (20%). The mixture was hydrogenated under 40 psi H2 at room temperature for 1 hour. The mixture was filtered over a celite, the celite pad was washed with CH3OH and the resulting solution was concentrated to yield 2.3 gm of 2-(6-((N-(3-(trifluoromethoxy)benzyl)-1-methyl-1H-imidazole-4-carboxamido)methyl)-3-aza-bicyclo[3.1.0]hexan-3-yl)acetic acid as a yellow solid; 400 MHz 1H NMR (CDCl3) δ 7.54 (s, 1H), 7.23-7.33 (m, 3H), 7.15 (s, 1H), 7.05 (d, J=7.9 Hz, 1H), 5.4 (brs, 2H), 4.81 (brs, 1H), 3.96 (brs, 1H), 3.68 (s, 3H), 3.49 (s, 2H), 3.28 (brs, 1H), 3.12 (brs, 2H), 1.76 (brs, 1H), 1.66 (brs, 2H); MS (M+1) 452.1.

Workup

  1. filtrationThe mixture was filtered over a celite
  2. washthe celite pad was washed with CH3OH
  3. concentrationthe resulting solution was concentrated

Sources & evidence

ORD record
ord-dab18566e7934afcada6985ab560d47e
Source dataset
uspto-grants-2012_02
Patent number
US08124639B2

Reaction notes

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