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

HRID 1039040노트

반응식

HRID 1039040 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 83717Copper iodide촉매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9e1cfd6971f640e68a52a873d1e587cb
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552032B2

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