Hydrochloric Acid → Methyl 1-(4-benzamidophenylamino)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylate

HRID 1029225

반응식

HRID 1029225 반응식
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:24][CH:23]=1.Cl>CN1C(=O)CCC1.O>[C:29]([NH:28][C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)=[CH:27][CH:26]=1)(=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 87196Benzamide, N-(4-aminophenyl)-HCID 58168369Methyl 1-chloro-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylate

생성물 1

HCID 44205292Methyl 1-(4-benzamidophenylamino)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylate수율 96%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
115 °C

실험 절차

266 (250 mg, 0.77 mol), N-(4-aminophenyl)benzamide (179 mg, 0.85 mmol), and HCl (19 μm, 0.77 mmol, 4.0 M in dioxane) were suspended in NMP (5 mL) and stirred for 30 h at 115° C. The reaction mixture was diluted with H2O. The resulting precipitate was filtered, washed with H2O and MeOH, and dried under vacuum to provide 267 (341 mg, 96% yield) as a white solid. LC-MS (M+H=465, obsd.=465).

후처리

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with H2O and MeOH
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-00a38f894260489c8c0ddaaace553e8a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735584B2

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