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Water → methyl 2-(1-methyl-5-(4-methyl-4-nitropentyloxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

HRID 246734
ノート
印刷プレビュー

反応式

HRID 246734 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[C:5]2[C:12]1[N:17]=[C:16]2[C:18]([C:40]([O:42][CH3:43])=[O:41])=[CH:19][N:20]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]2=[N:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:51][CH2:52][CH2:53][C:54]([CH3:59])([N+:56]([O-:58])=[O:57])[CH3:55].O>CN(C=O)C>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:51][CH2:52][CH2:53][C:54]([CH3:59])([N+:56]([O-:58])=[O:57])[CH3:55])=[CH:10][CH:9]=2)[C:5]([C:12]2[N:17]=[C:16]3[C:18]([C:40]([O:42][CH3:43])=[O:41])=[CH:19][N:20]([C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:15]3=[N:14][CH:13]=2)=[N:6]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 553015211-Chloro-4-methyl-4-nitropentaneHCID 71280393methyl 2-(5-hydroxy-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

生成物 1

HCID 71280089methyl 2-(1-methyl-5-(4-methyl-4-nitropentyloxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate収率 66.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of methyl 2-(5-hydroxy-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (2.2 g, 3.9 mmol) in DMF (25 mL) was added K2CO3 (1.8 g, 12.8 mmol) and 1-chloro-4-methyl-4-nitropentane (1.0 g, 5.9 mmol), after the addition, the reaction mixture was heated to 100° C. with stirring for 4 hours. The reaction mixture was cooled to room temperature, H2O (25 mL) was added and product extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to give methyl 2-(1-methyl-5-(4-methyl-4-nitropentyloxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (1.8 g, 66.7%) as yellow solid. LCMS: (M+H)+=695.

後処理

  1. additionafter the addition
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionproduct extracted with EtOAc (100 mL)
  4. washThe organic layer was washed with H2O (100 mL) and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7dfd75488c054b608237d6830793c8dd
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658646B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート