Methyl 3-amino-2,2-dimethylpropanoate → HCID 89813164, compound

HRID 1481132Notes

Reaction equation

HRID 1481132 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][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.[CH3:28][O:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][NH2:33]>CO>[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][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7]

Participants

4

Reactant 2

HCID 13285789Methyl 3-amino-2,2-dimethylpropanoateHCID 67110273HCID 67110273, compound

Product 1

HCID 89813164HCID 89813164, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (50 mg, 0.13 mmol) and 3-amino-2,2-dimethyl-propionic acid methyl ester (52 mg, 0.40 mmol) in MeOH (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 (0-40% EtOAc/hexanes+2% AcOH) to give 46 mg of the title compound. 1H NMR (CDCl3, 200 MHz): δ ppm=14.0 (s, 1H), 8.20-8.35 (m, 2H), 7.87 (d, 1H, J=1.2 Hz), 6.40-6.70 (m, 6H), 3.79 (s, 3H), 3.61 (d, 2H, J=7.0 Hz), 1.30 (s, 6H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (0-40% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-79f81f02da5c4077bdf028d331b95206
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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