HCID 178519342, compound → HCID 178519355, compound

HRID 2360941Notes

Reaction equation

HRID 2360941 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH:14]4[C:18]5[CH:19]=[C:20]([C:25]6[CH2:26][CH2:27][O:28][CH2:29][CH:30]=6)[CH:21]=[CH:22][C:23]=5[CH2:24][CH:13]34)=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1>[Pd].CO>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:12]3[CH2:17][CH2:16][CH2:15][C@@H:14]4[C:18]5[CH:19]=[C:20]([CH:25]6[CH2:26][CH2:27][O:28][CH2:29][CH2:30]6)[CH:21]=[CH:22][C:23]=5[CH2:24][C@H:13]34)=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 178519342HCID 178519342, compound

Product 1

HCID 178519355HCID 178519355, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1H-benzoimidazol-5-yl)-[6-(3,6-dihydro-2H-pyran-4-yl)-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl]-methanone (48 mg), 10% palladium on carbon (10 mg), and methanol (3 mL) is shaken under hydrogen atmosphere (5 bar) at room temperature overnight. The catalyst is then separated by filtration and the filtrate is concentrated. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:09:1) to afford the title compound. Yield: 15 mg (31% of theory); LC (method 1): tR=2.63 min; Mass spectrum (ESI+): m/z=402 [M+H]+.

Workup

  1. customThe catalyst is then separated by filtration
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:09:1)

Sources & evidence

ORD record
ord-cc588dbc43c8425fbdb882c2c03adb2b
Source dataset
uspto-grants-2014_04
Patent number
US08686149B2

Reaction notes

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