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tert-butyl (3R)-3-aminopiperidine-1-carboxylate → (R)-tert-butyl 3-(2-(5-(2,6-difluorophenyl)-1-tosyl-1H-indol-3-yl)pyrimidin-4-ylamino)piperidine-1-carboxylate

HRID 1529305
ノート
印刷プレビュー

反応式

HRID 1529305 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=4[F:24])[CH:15]=3)[N:10]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:9]=2)[N:3]=1.[NH2:35][C@@H:36]1[CH2:41][CH2:40][CH2:39][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:37]1>CS(C)=O>[F:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:17]=1[C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:25]([C:28]1[CH:29]=[CH:30][C:31]([CH3:32])=[CH:33][CH:34]=1)(=[O:27])=[O:26])[CH:9]=[C:8]2[C:4]1[N:3]=[C:2]([NH:35][C@@H:36]2[CH2:41][CH2:40][CH2:39][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:37]2)[CH:7]=[CH:6][N:5]=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

4

反応物 2

HCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 867097683-(4-chloropyrimidin-2-yl)-5-(2,6-difluorophenyl)-1-tosyl-1H-indole

生成物 1

HCID 67959582(R)-tert-butyl 3-(2-(5-(2,6-difluorophenyl)-1-tosyl-1H-indol-3-yl)pyrimidin-4-ylamino)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 3-(4-chloropyrimidin-2-yl)-5-(2,6-difluorophenyl)-1-tosyl-1H-indole (500 mg, 10 mmol) and (R)-tert-butyl 3-aminopiperidine-1-carboxylate (404 mg, 2.02 mmol) in DMSO (10 mL) was heated at 110° C. for 12 h. The resulting mixture was cooled to at RT for 2 h. The reaction mixture was quenched with ice cold water and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated to yield crude compound. Purification by silica gel column chromatography, eluting with 5-15% EtOAc and hexanes to the title compound (500 mg, 75%). MS (ESI, pos. ion) m/z: 660 (M+1).

後処理

  1. temperatureThe resulting mixture was cooled to at RT for 2 h
  2. customThe reaction mixture was quenched with ice cold water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield crude compound
  8. customPurification by silica gel column chromatography
  9. washeluting with 5-15% EtOAc and hexanes to the title compound (500 mg, 75%)

出典と根拠

ORDレコード
ord-e7d2af2e3bdf456a8bb11c7a7e981398
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090593B2

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