Ammonium Chloride → N'-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine

HRID 1842676노트

반응식

HRID 1842676 반응식
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21]([NH:26][C:27]4[CH:32]=[C:31]([N+:33]([O-])=O)[C:30]([C:36]5[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH:41]=5)=[CH:29][C:28]=4[O:43][CH3:44])[N:20]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21]([NH:26][C:27]4[CH:32]=[C:31]([NH2:33])[C:30]([C:36]5[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH:41]=5)=[CH:29][C:28]=4[O:43][CH3:44])[N:20]=3)=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 71239353HCID 71239353, 화합물2회

생성물 1

HCID 86677326N'-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine수율 140.2%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

A mixture of 4-[1-(benzenesulfonyl)indol-3-yl]-5-chloro-N-[2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitrophenyl]pyrimidin-2-amine (Intermediate 9, 349 mg, 0.47 mmol), iron (157 mg, 2.82 mmol) and NH4Cl (17.60 mg, 0.33 mmol) in ethanol (9 mL) and water (3 mL) was heated at reflux for 1.5 h. The mixture was cooled and concentrated in vacuo. CH2Cl2 (20 mL) and CH3OH (2 mL) were then added and the mixture was stirred for 5 minutes and then filtered. The organic solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (396 mg, 140%) as a green foam which was used without further purification. m/z: ES+ MH+ 601.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. additionCH2Cl2 (20 mL) and CH3OH (2 mL) were then added
  6. filtrationfiltered
  7. washThe organic solution was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-39656e78de5f4644ac38e7f2baaa35cf
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946235B2

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