HCID 178519342, compound → HCID 178519355, compound

HRID 455510Notes

Reaction equation

HRID 455510 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 1:0→9:1) 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 1:0→9:1)

Sources & evidence

ORD record
ord-c4853d4d486c4577b30f170b38251130
Source dataset
uspto-grants-2013_07
Patent number
US08497281B2

Reaction notes

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