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1,2-Dichloroethane → 3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-N-piperidin-2-ylmethyl-benzamide

HRID 14761
ノート
印刷プレビュー

反応式

HRID 14761 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=O)[CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.C(OC([N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[CH2:39][NH2:40])=O)(C)(C)C.C(Cl)CCl>CN(C=O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([NH:40][CH2:39][CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][NH:33]3)=[O:22])[CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 111,2-DichloroethaneHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylateHCID 670445203-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

生成物 1

HCID 586035553-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-N-piperidin-2-ylmethyl-benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Intermediate 9 (1 mmol) was coupled with 2-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (3 mmol) using EDC (2 mmol) in DMF (10 mL). The DMF was removed by rotary evaporation and the residue purified by flash chromatography on silica gel (ethyl acetate as eluent.) The resulting product was deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 432. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.5-8.65 (m, 2H) 8.38 (m, 1H) 8.22 (m, 1H) 7.95 (m, 1H) 7.55 (m, 1H) 7.28 (m, 1H) 7.20 (d, 1H) 7.05 (d, 2H) 6.68 (d, 2H) 3.5 (m, 2H) 3.3 (m, 2H) 2.95 (m, 1H) 2.6-2.85 (m, 3H) 2.48 (m, 1H) 1.0-1.7 (m, 6H).

後処理

  1. customThe DMF was removed by rotary evaporation
  2. customthe residue purified by flash chromatography on silica gel (ethyl acetate as eluent.) The resulting product

出典と根拠

ORDレコード
ord-96a7a6d2860e45e4bb93749ba9697cf2
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07732444B2

反応ノート

読み込み中…

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