HCID 117877602, compound → HCID 117877607, compound

HRID 922484Notes

Reaction equation

HRID 922484 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:27]1[CH2:29][CH2:28]1)[CH:9]([C:11]1[CH:12]=[C:13]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:26])[O:24][CH3:25])[C:14]([CH:17]=[CH2:18])=[N:15][CH:16]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]([CH:27]1[CH2:28][CH2:29]1)[CH:9]([C:11]1[CH:12]=[C:13]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:26])[O:24][CH3:25])[C:14]([CH2:17][CH3:18])=[N:15][CH:16]=1)[CH3:10])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 117877602HCID 117877602, compound

Product 1

HCID 117877607HCID 117877607, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

to a solution of methyl [3-(5-{1-[(tert-butoxycarbonyl)(cyclopropyl)amino]ethyl}-2-vinylpyridin-3-yl)propyl]carbamate (280 mg) in methanol (10 mL) was added 10% palladium on carbon (140 mg), and the mixture was stirred under hydrogen for 2 hours. An insoluble was filtered off, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform→chloroform/methanol=4/1) to give methyl [3-(5-{1-[(tert-butoxycarbonyl)(cyclopropyl)amino]-ethyl}-2-ethylpyridin-3-yl)propyl]carbamate [REx(113-7)] (210 mg) as a pale yellow oil.

Workup

  1. filtrationAn insoluble was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform→chloroform/methanol=4/1)

Sources & evidence

ORD record
ord-7af444956ea94767b8cb2ee1183e1552
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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