N-(3-{5-[3-(Formamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)formamide → N-(3-{5-[3-(Formylamino)propyl]pyridin-2-yl}propyl)formamide

HRID 49576Notes

Reaction equation

HRID 49576 reaction equation
[CH:1]([NH:3][CH2:4][C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][NH:16][CH:17]=[O:18])=[N:11][CH:12]=1)=[O:2]>CO>[CH:1]([NH:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][NH:16][CH:17]=[O:18])=[N:11][CH:12]=1)=[O:2]

Participants

3

Reactant 1

HCID 11413798N-(3-{5-[3-(Formamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)formamide

Product 1

HCID 11161008N-(3-{5-[3-(Formylamino)propyl]pyridin-2-yl}propyl)formamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(3-{5-[3-(formamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)formamide (9-1) (28 g) and 5% Pd/Al2O3 (2.8 g) in methanol (350 mL) was hydrogenated at 40 psi at ambient temperature for 5 h. The mixture was filtered through Solka Floc. The filtrate was concentrated to afford 13-1 as an oil.

Workup

  1. filtrationThe mixture was filtered through Solka Floc
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e2477c57cb5a49bc93b3462d5be5734f
Source dataset
uspto-grants-2004_03
Patent number
US06706885B2

Reaction notes

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