Diethylamine → {5-[2-Amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-methyl-carbamic acid tert-butyl ester

HRID 1039040ノート

反応式

HRID 1039040 の反応式
[C:1]([O:5][C:6](=[O:14])[N:7]([CH3:13])[CH2:8][CH2:9][CH2:10][C:11]#[CH:12])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:34]=[CH:33][C:19]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)=[O:21])=[CH:18][C:17]=1I.C(NCC)C>[Cu](I)I>[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:8][CH2:9][CH2:10][C:11]#[C:12][C:17]1[CH:18]=[C:19]([C:20](=[O:21])[NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)[CH:33]=[CH:34][C:16]=1[NH2:15])[CH3:13])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8021DiethylamineHCID 672356514-amino-N-(3,4-dimethoxyphenyl)-3-iodobenzamideHCID 86654758Tert-butyl methyl(pent-4-yn-1-yl)carbamate

生成物 1

HCID 67236460{5-[2-Amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-methyl-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 83717Copper iodide触媒

実験手順

A 500 mL round bottom flask was charged with methyl-pent-4-ynyl-carbamic acid tert-butyl ester (1.70 g, 8.62 mmol), 4-amino-N-(3,4-dimethoxyphenyl)-3-iodobenzamide (3.0 g, 7.53 mmol), copper iodide (0.225 g, 1.18 mmol), palladium tetrakistriphenylphosphine (0.93 g, 0.805 mmol), and diethylamine (258 mL) and the resulting mixture stirred at room temperature for 24 h. The resulting mixture was then concentrated in vacuo and the residue purified via flash silica gel chromatography (Analogix IF-280, SF40-400 g column, gradient 90:10-10:90 Heptane:EtOAc) to yield {5-[2-amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-methyl-carbamic acid tert-butyl ester. MS (ES+) 468 (M+1).

後処理

  1. concentrationThe resulting mixture was then concentrated in vacuo
  2. customthe residue purified via flash silica gel chromatography (Analogix IF-280

出典と根拠

ORDレコード
ord-9e1cfd6971f640e68a52a873d1e587cb
出典データセット
uspto-grants-2013_10
特許番号
US08552032B2

反応ノート

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