Pivaloyl chloride → Ethyl 1-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]piperidin-4-carboxylate

HRID 1582962

Reaction equation

HRID 1582962 reaction equation
C(O[C:9]([CH2:11][N:12]1[CH2:22][CH2:21][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13]1)=[O:10])C1C=CC=CC=1.C[O-].[Na+].C(Cl)(=O)C(C)(C)C.[Cl:33][C:34]1[CH:35]=[C:36]([CH:49]=[CH:50][CH:51]=1)[C:37]([C:39]1[C:40]([NH:46][CH2:47][CH3:48])=[N:41][C:42]([CH3:45])=[CH:43][CH:44]=1)=O>C(O)C.C1COCC1.[C].[Pd]>[Cl:33][C:34]1[CH:35]=[C:36]([C:37]2[C:39]3[C:40](=[N:41][C:42]([CH3:45])=[CH:43][CH:44]=3)[N:46]([CH2:47][CH3:48])[C:9](=[O:10])[C:11]=2[N:12]2[CH2:13][CH2:14][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:21][CH2:22]2)[CH:49]=[CH:50][CH:51]=1

Participants

8

Reactant 4

HCID 62493Pivaloyl chlorideHCID 10942334Sodium Methoxide2×HCID 110549023-(3-Chlorobenzoyl)-2-ethylamino-6-methylpyridineHCID 22716663Ethyl 1-(benzyloxycarbonylmethyl)isonipecotate

Product 1

HCID 22716665Ethyl 1-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]piperidin-4-carboxylate

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(benzyloxycarbonylmethyl)isonipecotate was subjected to catalytic reduction under a hydrogen atmosphere of 1 atm in ethanol in the presence of 10% palladium-carbon. The resulting compound was treated with sodium methoxide in ethanol and then reacted with pivaloyl chloride in THF. The resulting compound was reacted with 3-(3-chlorobenzoyl)-2-ethylamino-6-methylpyridine under heating, and further treated with sodium methoxide in ethanol. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain ethyl 1-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]piperidin-4-carboxylate as a yellow oily substance. MS: 454.

Workup

  1. temperatureunder heating
  2. custompurified in a usual manner

Sources & evidence

ORD record
ord-ec34bd55d9814f0c9662c607106c0a73
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Linked notes

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