HCID 178519342, compound → HCID 178519355, compound

HRID 521169Notes

Reaction equation

HRID 521169 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-021c962a74014f3991407596bf542643
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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