Methyl 3-amino-2,2-dimethylpropanoate → HCID 89812874, compound

HRID 1481139Notes

Reaction equation

HRID 1481139 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:26]#[N:27])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])CCC.[CH3:28][O:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][NH2:33]>CCO>[CH3:28][O:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][NH:33][C:6]([C:8]1[N:9]=[C:10]([C:26]#[N:27])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7]

Participants

4

Reactant 2

HCID 13285789Methyl 3-amino-2,2-dimethylpropanoateHCID 67110485HCID 67110485, compound

Product 1

HCID 89812874HCID 89812874, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-6-phenoxy-isoquinoline-3-carboxylic acid butyl ester (50 mg, 0.14 mmol) (prepared according to U.S. Pat. No. 7,928,120) and 3-amino-2,2-dimethyl-propionic acid methyl ester (90 mg, 0.70 mmol) in EtOH (2 mL) was heated at 150° C. in a microwave reactor for 3 h. The solvent was evaporated, and the residue was purified by column chromatography (0-30% EtOAc/hexanes) to give 38 mg of the title compound. 1H NMR (CDCl3, 200 MHz): δ ppm=13.9 (s, 1H), 8.20-8.40 (m, 2H), 7.10-7.70 (m, 7H), 3.79 (s, 3H), 3.62 (d, 2H, J=7.0 Hz), 1.30 (s, 6H).

Workup

  1. customprepared
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-217dc465319f435395be2008d75f8787
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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