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

HRID 1039040Notes

Reaction equation

HRID 1039040 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-9e1cfd6971f640e68a52a873d1e587cb
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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