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Water → Tert-butyl 4-[2'-(2-{[(cyanomethyl)amino]carbonyl}-4-methylpentyl)[1,1'-biphenyl]-4-yl]-1-piperazinecarboxylate

HRID 1744073
ノート
印刷プレビュー

反応式

HRID 1744073 の反応式
Br[C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][CH:5]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([NH:8][CH2:9][C:10]#[N:11])=[O:7].[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:10]([CH2:9][NH:8][C:6]([CH:5]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:4][C:3]1[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=1[C:36]1[CH:35]=[CH:34][C:33]([N:30]2[CH2:29][CH2:28][N:27]([C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[CH2:32][CH2:31]2)=[CH:38][CH:37]=1)=[O:7])#[N:11]
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

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 52330144-(4-BOC-Piperazino)phenylboronic acidHCID 222361892-(2-bromobenzyl)-N-(cyanomethyl)-4-methylpentanamide

生成物 1

HCID 22235962Tert-butyl 4-[2'-(2-{[(cyanomethyl)amino]carbonyl}-4-methylpentyl)[1,1'-biphenyl]-4-yl]-1-piperazinecarboxylate

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
2 回
HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To 2-(2-bromobenzyl)-N-(cyanomethyl)-4-methylpentanamide (260 mg, 0.805 mmol) and 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (275 mg, 0.886 mmol) in DMF (10 mL) under dry nitrogen was added aqueous sodium carbonate (2 M, 1.2 mL, 2.42 mmol) followed by the catalyst PdCl2(dppf) (25 mg, 0.025 mmol). The reaction was heated to 90° C. for 0.5 hours and more PdCl2(dppf) (25 mg, 0.025 mmol) was added and the reaction mixture was heated for another 4 hours. Water was added and the product extracted with ether (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 35/65) to afford tert-butyl 4-[2′-(2-{[(cyanomethyl)amino]carbonyl}-4-methylpentyl)[1,1 ′-biphenyl]-4-yl]-1-piperazinecarboxylate.

後処理

  1. temperaturethe reaction mixture was heated for another 4 hours
  2. extractionthe product extracted with ether (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography over silica gel (EtOAc/Hex, 35/65)

出典と根拠

ORDレコード
ord-7a6f68e372b1441dbc2a21c8b365f9e8
出典データセット
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07012075B2

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