Oxalyl chloride → HCID 86615153, compound

HRID 2366713Notes

Reaction equation

HRID 2366713 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH2:7]([C:10]1[N:11]([CH2:23][CH2:24][CH2:25][CH2:26]CC(O)=O)[C:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1)[CH2:8][CH3:9]>ClCCl.CN(C=O)C>[CH2:7]([C:10]1[N:11]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:1][C:2]([Cl:4])=[O:3])[C:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1)[CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 65578Oxalyl chloride2×HCID 69506746HCID 69506746, compound

Product 1

HCID 86615153HCID 86615153, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (2.04 mL, 23.4 mmol) in dichloromethane (15 mL) was added dropwise to a suspension of 6-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]hexanoic acid (2.56 g, 7.8 mmol) in dichloromethane (38 mL) containing one drop of DMF. The reaction mixture was stirred at ambient temperature for 1.75 hours, and then additional oxalyl chloride (0.35 mL, 4.1 mmol) was added. The reaction was stirred for an additional 45 minutes and then concentrated under reduced pressure to provide 6-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]hexanoyl chloride.

Workup

  1. stirringThe reaction was stirred for an additional 45 minutes
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5da68acaafd64e2b9f926923757e8f6b
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…