HCID 178519369, compound → HCID 178507196, compound

HRID 521173Notes

Reaction equation

HRID 521173 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][C@@H:14]4[C:18]5[CH:19]=[C:20]([OH:28])[C:21]([N+:25]([O-])=O)=[CH:22][C:23]=5[CH2:24][C@H:13]34)=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1>[Pd].CO>[NH2:25][C:21]1[C:20]([OH:28])=[CH:19][C:18]2[C@@H:14]3[C@@H:13]([N:12]([C:10]([C:8]4[CH:7]=[CH:6][C:5]5[NH:1][CH:2]=[N:3][C:4]=5[CH:9]=4)=[O:11])[CH2:17][CH2:16][CH2:15]3)[CH2:24][C:23]=2[CH:22]=1

Participants

4

Reactant 1

HCID 178519369HCID 178519369, compound

Product 1

HCID 178507196HCID 178507196, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1H-benzoimidazol-5-yl)-(cis-6-hydroxy-7-nitro-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-methanone (0.56 g), 10% palladium on carbon (50 mg), and methanol (10 mL) is shaken under hydrogen atmosphere (1 bar) at room temperature for 3 h. The catalyst is separated by filtration and the filtrate is concentrated. The residue is chromatographed (dichloromethane/methanol 1:1→7:3) to give the title compound. Yield: 0.32 g (63% of theory); LC (method 1): tR=0.65 min; Mass spectrum (ESI+): m/z=349 [M+H]+.

Workup

  1. customThe catalyst is separated by filtration
  2. concentrationthe filtrate is concentrated
  3. customThe residue is chromatographed (dichloromethane/methanol 1:1→7:3)

Sources & evidence

ORD record
ord-d6fb8993d6f74e5fa909e6cc7c2df593
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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