HCID 178498470, compound → HCID 178498427, compound

HRID 1807854Notes

Reaction equation

HRID 1807854 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[N:16]([C:20]3[C:29]([N+:30]([O-])=O)=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([CH3:33])[CH:21]=3)[CH:17]=[CH:18][N:19]=2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:30][C:29]1[C:20]([N:16]2[CH:17]=[CH:18][N:19]=[C:15]2[C@H:12]2[CH2:13][CH2:14][C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH2:10][CH2:11]2)=[CH:21][C:22]([CH3:33])=[C:23]([CH:28]=1)[C:24]([O:26][CH3:27])=[O:25]

Participants

4

Reactant 1

HCID 178498470HCID 178498470, compound

Product 1

HCID 178498427HCID 178498427, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.05 g of the yellow solid having methyl 4-[2-(cis-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-imidazol-1-yl]-2-methyl-5-nitrobenzoate obtained as a low-polarity compound in 15 mL of methanol was added 0.40 g of 10% palladium on carbon (50% wet), followed by stirring overnight under a hydrogen atmosphere. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 0.62 g of methyl 5-amino-4-[2-(cis-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-imidazol-1-yl]-2-methylbenzoate as a yellow oily substance.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Sources & evidence

ORD record
ord-498f6d873bb64399a3d028a2cac45056
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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