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Ammonium Chloride → 4-(3-Dimethylaminoazetidin-1-yl)-6-methoxy-N-[4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,3-diamine

HRID 1842770
ノート
印刷プレビュー

反応式

HRID 1842770 の反応式
[CH3:1][N:2]([CH3:35])[CH:3]1[CH2:6][N:5]([C:7]2[C:12]([N+:13]([O-])=O)=[CH:11][C:10]([NH:16][C:17]3[N:22]=[C:21]([C:23]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]([CH3:32])[CH:24]=4)[CH:20]=[CH:19][N:18]=3)=[C:9]([O:33][CH3:34])[CH:8]=2)[CH2:4]1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[CH3:35][N:2]([CH3:1])[CH:3]1[CH2:4][N:5]([C:7]2[CH:8]=[C:9]([O:33][CH3:34])[C:10]([NH:16][C:17]3[N:22]=[C:21]([C:23]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]([CH3:32])[CH:24]=4)[CH:20]=[CH:19][N:18]=3)=[CH:11][C:12]=2[NH2:13])[CH2:6]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 71240795N-[4-(3-dimethylaminoazetidin-1-yl)-2-methoxy-5-nitrophenyl]-4-(1-methylindol-3-yl)pyrimidin-2-amine2 回

生成物 1

HCID 866773434-(3-Dimethylaminoazetidin-1-yl)-6-methoxy-N-[4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,3-diamine収率 80%

試薬・触媒・溶媒 3

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

実験手順

A mixture of N-[4-(3-dimethylaminoazetidin-1-yl)-2-methoxy-5-nitrophenyl]-4-(1-methylindol-3-yl)pyrimidin-2-amine (Intermediate 117, 160 mg, 0.34 mmol), iron (113 mg, 2.03 mmol) and NH4Cl (13.56 mg, 0.25 mmol) in ethanol (5 mL) and water (1.67 mL) was heated at reflux for 2 h. The cooled mixture was purified by ion exchange chromatography, using an SCX column and eluting with 1:1 7M methanolic ammonia in CH2Cl2. Appropriate fractions were combined and concentrated in vacuo. Further purification by FCC, eluting with 0-5% 7N methanolic ammonia in CH2Cl2 gave the title compound (120 mg, 80%) as a brown gum; m/z: ES+ MH+ 444.61.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customThe cooled mixture was purified by ion exchange chromatography
  4. washeluting with 1:1 7M methanolic ammonia in CH2Cl2
  5. concentrationconcentrated in vacuo
  6. customFurther purification by FCC
  7. washeluting with 0-5% 7N methanolic ammonia in CH2Cl2

出典と根拠

ORDレコード
ord-98b50e8df47844d1b721550de7c55c8f
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946235B2

反応ノート

読み込み中…

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