4-Cyanobutanoic acid → 4-(3-chlorophenyl)-3-(2-cyanoethyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one

HRID 1582958

Reaction equation

HRID 1582958 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]([OH:8])=O)#[N:2].C[O-].[Na+].C(Cl)(=O)C(C)(C)C.[Cl:19][C:20]1[CH:21]=[C:22]([CH:35]=[CH:36][CH:37]=1)[C:23]([C:25]1[C:26]([NH:32][CH2:33][CH3:34])=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=1)=O>CO.C1COCC1.C(O)C>[Cl:19][C:20]1[CH:21]=[C:22]([C:23]2[C:25]3[C:26](=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=3)[N:32]([CH2:33][CH3:34])[C:6](=[O:8])[C:5]=2[CH2:4][CH2:3][C:1]#[N:2])[CH:35]=[CH:36][CH:37]=1

Participants

8

Reactant 4

HCID 382394-Cyanobutanoic acidHCID 62493Pivaloyl chlorideHCID 10942334Sodium Methoxide2×HCID 110549023-(3-Chlorobenzoyl)-2-ethylamino-6-methylpyridine

Product 1

HCID 129911884-(3-chlorophenyl)-3-(2-cyanoethyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

After the treatment of 4-cyanobutanoic acid with sodium methoxide in methanol, the treated compound was reacted with pivaloyl chloride in THF. Thus obtained compound was reacted with 3-(3-chlorobenzoyl)-2-ethylamino-6-methylpyridine under heating. Then, the compound obtained by usual work-up was reacted in ethanol in the presence of sodium methoxide under heating. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain 4-(3-chlorophenyl)-3-(2-cyanoethyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one as a pale yellow solid. MS: 352.

Workup

  1. temperatureunder heating
  2. customThen, the compound obtained by usual work-up
  3. temperatureunder heating
  4. custompurified in a usual manner

Sources & evidence

ORD record
ord-d654fb4d8c834d78a26cd3595d5d459f
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Linked notes

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