Oxalyl chloride → HCID 57455391, compound

HRID 1623102Notes

Reaction equation

HRID 1623102 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].C(Cl)(=O)C([Cl:27])=O>CN(C)C=O.ClCCl>[CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21]([Cl:27])=[O:23])[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 57455390HCID 57455390, compound

Product 1

HCID 57455391HCID 57455391, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

One drop of N,N-dimethylformamide (DMF) was added to a solution of 4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyric acid (3.53 g, 11.3 mmol, 1.0 eq) in dichloromethane (55 mL). Oxalyl chloride (3.0 mL, 33.9 mmol, 3.0 eq) was added dropwise over 5 minutes to the reaction mixture, which was subsequently stirred for 2 hours at ambient temperature. The mixture was concentrated under reduced pressure to provide 4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyryl chloride.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a1c5fe6a6c594ceea1f7806a307348cb
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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