HCID 11449562, compound → HCID 72806257, compound

HRID 2271357Notes

Reaction equation

HRID 2271357 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]([CH2:5][CH2:6][CH2:7][C:8]#[C:9][C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[C:13]([NH:15][CH2:16][CH2:17][F:18])=[O:14])=[O:4]>[Ni]>[CH3:22][N:2]([CH3:1])[C:3]([CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[C:13]([NH:15][CH2:16][CH2:17][F:18])=[O:14])=[O:4]

Participants

3

Reactant 1

HCID 11449562HCID 11449562, compound

Product 1

HCID 72806257HCID 72806257, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Hydrogenation of 3-(5-dimethylcarbamoyl-pent-1-ynyl)-N-(2-fluoro-ethyl)benzamide (26) (0.040 g, 0.13 mmol) using BER/Ni catalyst gave 40% 28, and 55% of starting material. The mixture was separated by reverse-phase HPLC chromatography (30% acetonitrile/70% water 20 min isocratic program) to give 3-(5-dimethylcarbamoyl-pent-1-enyl)-N-(2-fluoro-ethyl)-benzamide 28 (5 mg).

Sources & evidence

ORD record
ord-c9b2cf240a3e405da87a91674eaf7eed
Source dataset
uspto-grants-2015_09
Patent number
US09120723B2

Reaction notes

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