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

反応式

HRID 1842737 の反応式
[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

参加物

8

反応物 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-diamine2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c67e5c78739c47738912c9b710add88c
出典データセット
uspto-grants-2015_02
特許番号
US08946235B2

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