Ammonia → HCID 22716668, compound

HRID 1582969Notes

Reaction equation

HRID 1582969 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[CH2:22][CH2:23][CH2:24][C:25]([OH:27])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[NH3:34]>CN(C=O)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[CH2:22][CH2:23][CH2:24][C:25]([NH2:34])=[O:27])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 22716703HCID 22716703, compound

Product 1

HCID 22716668HCID 22716668, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a THF solution of 4-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]butanoic acid were added oxalyl chloride and one drop of DMF, followed by stirring at room temperature. The reaction mixture was added dropwise to an ice-cooled THF solution of concentrated aqueous ammonia and then, the whole was stirred for 30 minutes. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain 4-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]butanamide. To a dichloroethane solution of the resulting compound were added pyridine, phosphorus oxychloride and one drop of DMF, followed by stirring at room temperature. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain 4-(3-chlorophenyl)-3-(3-cyanopropyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one. NMR1: 6.90 (1H, d, J=8.2 Hz), 4.67 (2H, q, J=7.1 Hz), 1.70-2.10 (2H, m).

Workup

  1. stirringthe whole was stirred for 30 minutes
  2. custompurified in a usual manner

Sources & evidence

ORD record
ord-4e47f9996b4547aeb838a9cb37c60f40
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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