Ethyl 3-amino-2,2-dimethylpropanoate → HCID 89813081, compound

HRID 1481060Notes

Reaction equation

HRID 1481060 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH3:24])[CH:9]=2)=[O:4].[CH2:27]([O:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][NH2:33])[CH3:28]>C(O)C>[CH2:27]([O:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][NH:33][C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH3:24])[CH:9]=2)=[O:4])[CH3:28]

Participants

4

Reactant 2

HCID 421529Ethyl 3-amino-2,2-dimethylpropanoateHCID 89813171HCID 89813171, compound

Product 1

HCID 89813081HCID 89813081, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-Cyano-7-(2-ethyl-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.14 mmole) and 3-amino-2,2-dimethyl-propionic acid ethyl ester (41 mg, 0.43 mmole) in anhydrous ethanol (0.7 ml) was stirred at 130° C. for two hours and 150° C. for one hour before it was cooled to room temperature, concentrated and by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a colorless oil (20.3 mg): MS: (+) m/z 462.22 (M+1), (−) m/z 460.10 (M−1).

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated and by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-3235ba914a144c88918aaafbac0668fa
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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