Potassium Carbonate → 7-chloro-3-(3,5-dimethoxyphenyl)-1,8-dimethyl-1,6-naphthyridin-2(1H)-one

HRID 524067

반응식

HRID 524067 반응식
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([NH:11][CH3:12])[C:5]([CH:6]=O)=[CH:4][N:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][C:24](OC)=[O:25])[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]2[C:5]([CH:6]=[C:23]([C:17]3[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=[C:15]([O:14][CH3:13])[CH:16]=3)[C:24](=[O:25])[N:11]2[CH3:12])=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 592191Methyl 3,5-dimethoxyphenylacetateHCID 867135906-Chloro-5-methyl-4-(methylamino)nicotinaldehyde

생성물 1

HCID 867135917-chloro-3-(3,5-dimethoxyphenyl)-1,8-dimethyl-1,6-naphthyridin-2(1H)-one수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
105 °C

실험 절차

A mixture of 6-chloro-5-methyl-4-(methylamino)nicotinaldehyde (3.11 g, 16.8 mmol), methyl 2-(3,5-dimethoxyphenyl)acetate (4.25 g, 20.2 mmol) and potassium carbonate (2.8 g, 20.3 mmol) in N,N-dimethylformamide (100 mL) was stirred at 105° C. overnight. LCMS monitored the reaction was completed. The reaction mixture was cooled to RT and quenched by water. The precipitate was filtered and dried to get the title compound (5.5 g, crude) as a yellow solid. MS (ES+) C18H17ClN2O3 requires: 344, 346. found: 345, 347 [M+H]+.

후처리

  1. temperatureThe reaction mixture was cooled to RT
  2. customquenched by water
  3. filtrationThe precipitate was filtered
  4. customdried

출처 및 근거

ORD 기록
ord-b5d4d1ac9f7148c394290c2b063189d3
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340514B2

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