P-Anisidine → Ethyl 6-methoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate

HRID 1956429노트

반응식

HRID 1956429 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:13][O:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:2]2[NH:25][C:24]1[CH:26]=[CH:27][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 7732P-Anisidine2회HCID 11430Potassium Carbonate2회HCID 23209173Ethyl 4-chloro-6-methoxy-1,5-naphthyridine-3-carboxylate

생성물 1

HCID 23209166Ethyl 6-methoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of ethyl 4-chloro-6-methoxy-1,5-naphthyridine-3-carboxylate (1.68 g), 4-methoxyaniline (0.78 g), dry THF (50 ml) and anhydrous potassium carbonate (1.74 g) was stirred at ambient temperature for 7 hours. Further amounts of 4-methoxyaniline (0.4 g) and anhydrous potassium carbonate (0.9 g) were added and the mixture stirred at ambient temperature for 32 hours. The mixture was evaporated to dryness and the residue diluted with water (100 ml). The mixture was extracted into dichloromethane to give an oil which solidified. The solid was purified by column chromatography on silica using ethyl acetate as the mobile phase to give ethyl 6-methoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate, m.p. 115°-117° C.

후처리

  1. stirringthe mixture stirred at ambient temperature for 32 hours
  2. customThe mixture was evaporated to dryness
  3. additionthe residue diluted with water (100 ml)
  4. extractionThe mixture was extracted into dichloromethane
  5. customto give an oil which
  6. customThe solid was purified by column chromatography on silica

출처 및 근거

ORD 기록
ord-c6946770221947b9b3867228578e2fa6
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05780482

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