Methanol → N1-(2-dimethylaminoethyl)-5-methoxy-N1-methyl-N4-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine

HRID 1842737

반응식

HRID 1842737 반응식
[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][N:5]([CH3:35])[C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[CH:23]=3)[C:19]([CH3:32])=[CH:18][N:17]=2)=[C:8]([O:33][CH3:34])[CH:7]=1.[NH4+].[Cl-].C(Cl)Cl.CO>C(O)C.O.[Fe]>[CH3:36][N:2]([CH3:1])[CH2:3][CH2:4][N:5]([CH3:35])[C:6]1[C:11]([NH2:12])=[CH:10][C:9]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[CH:23]=3)[C:19]([CH3:32])=[CH:18][N:17]=2)=[C:8]([O:33][CH3:34])[CH:7]=1

참가 물질

8

반응물 4

HCID 887MethanolHCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 71270206N'-(2-Dimethylaminoethyl)-2-methoxy-N'-methyl-N-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]-5-nitrobenzene-1,4-diamine2회

생성물 1

HCID 86677254N1-(2-dimethylaminoethyl)-5-methoxy-N1-methyl-N4-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine수율 78%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

A mixture of N′-(2-dimethylaminoethyl)-2-methoxy-N′-methyl-N-[5-methyl-4-(1-methy-lindol-3-yl)pyrimidin-2-yl]-5-nitrobenzene-1,4-diamine (Intermediate 82, 202 mg, 0.41 mmol), iron (138 mg, 2.48 mmol) and NH4Cl (15.45 mg, 0.29 mmol) in ethanol (16 mL) and water (5.33 mL) was heated at reflux for 3 h. The mixture was then cooled and concentrated in vacuo to give a thick slurry. CH2Cl2 (100 mL) and CH3OH (10 mL) was then added and the mixture was stirred for 0.25 h and then filtered. The filter cake was washed further with CH2Cl2 and CH3OH and the combined organics were dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 1-8% methanolic ammonia in CH2Cl2 gave the title compound (147 mg, 78%) as a yellow dry film; m/z: ES+ MH+ 460.36.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated in vacuo
  5. customto give a thick slurry
  6. filtrationfiltered
  7. washThe filter cake was washed further with CH2Cl2 and CH3OH
  8. dry with materialthe combined organics were dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customPurification by FCC
  11. washeluting with 1-8% methanolic ammonia in CH2Cl2

출처 및 근거

ORD 기록
ord-c67e5c78739c47738912c9b710add88c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946235B2

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