Dimethylformamide → HCID 87235675, compound

HRID 2194489Notes

Reaction equation

HRID 2194489 reaction equation
[CH2:1]([S:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[CH:8]=[C:7]([C:15](O)=[O:16])[C:6]1=[O:18])[CH3:2].C(Cl)(=O)C([Cl:22])=O.CN(C)C=O>ClCCl>[CH2:1]([S:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[CH:8]=[C:7]([C:15]([Cl:22])=[O:16])[C:6]1=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 67009554HCID 67009554, compound

Product 1

HCID 87235675HCID 87235675, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.20 g (8.3 mmol) of 1-(ethylthiomethyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid was dissolved in dichloromethane (80 mL), and 5.0 mL (60 mmol) of oxalyl chloride was added thereto. One droplet of N,N-dimethylformamide was added to the above mixture, and the resulting mixture was stirred for one hour at room temperature. The reaction solution was concentrated under reduced pressure, and thus 1-(ethylthiomethyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid chloride was obtained. The acid chloride thus obtained was dissolved in dichloromethane (80 mL), and 1.02 g (9.1 mmol) of 1,3-cyclohexanedione and 1.40 mL (10.0 mmol) of triethylamine were added to the above solution under ice cooling. The resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into an aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with dichloromethane. The organic phase was dried and concentrated. The residue was washed with diisopropyl ether, and 2.99 g of the title compound was obtained as a light yellow solid (yield: quantitative).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-04c5363b98b04c30bfdaba4b2ba4ebb2
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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