Ammonia → HCID 11471419, compound

HRID 2361758Notes

Reaction equation

HRID 2361758 reaction equation
[C:1]1([CH2:7][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH:18]=[N:19][NH:20][CH:21]=3)[CH:12]=2)[C:9]#[N:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N.O.[H][H]>C(O)C.[Ni]>[C:1]1([CH2:7][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH:18]=[N:19][NH:20][CH:21]=3)[CH:12]=2)[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 113002733-Phenyl-2-[3-(1H-pyrazol-4-yl)-phenyl]-propionitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 11471419HCID 11471419, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of Example 2 (70 mg, 0.256 mmol, 1.0 equiv) in ethanol (25 ml) was added concentrated ammonia (0.5 ml) and Raney Nickel (approximately 0.5 ml of the water suspension) and the reaction mixture was subjected to a hydrogen atmosphere for 17 hours. The mixture was filtered through Celite® and the mother liquor was concentrated under reduced pressure to give the title compound which was purified by preparative liquid chromatography. (LC/MS: (PS-A) Rt 1.89 [M+H]+ 278.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe mother liquor was concentrated under reduced pressure

Sources & evidence

ORD record
ord-130e13dca855497d9b184733534b0efd
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

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