Diisopropylethylamine → 2,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamide

HRID 1029144

반응식

HRID 1029144 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1.[Cl:24][C:25]1[N:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:26]=1[C:27](Cl)=[O:28].CCN(C(C)C)C(C)C>O1CCOCC1.CCOC(C)=O.O>[Cl:24][C:25]1[N:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:26]=1[C:27]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1)=[O:28]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 27999962,5-Dichloro-nicotinoyl chlorideHCID 581683671-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

생성물 1

HCID 581683272,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamide수율 64.5%

시약·촉매·용매 2

HCID 312751,4-Dioxane용매HCID 22728543Water ethylacetate용매

실험 절차

Compound 137 (40 mg, 0.13 mmol), 2,5-dichloro-nicotinoyl chloride (28 mg, 0.13 mmol), and DIEA (0.02 mL, 0.13 mmol) were suspended in dioxane (2 mL), and stirred overnight at room temperature. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 180 (40 mg, 64% yield) as a white solid. LC-MS (M+H=478, obsd.=478).

후처리

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with EtOAc/H2O
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-6086b94094634432a2e6dc0c1eea5f42
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735584B2

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