Methyl 3-amino-2,2-dimethylpropanoate → 3-[(1-Cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid methyl ester

HRID 1481137Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.15 mmol) and 3-amino-2,2-dimethyl-propionic acid methyl ester (99 mg, 0.75 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 (0-25% EtOAc/hexanes) to give 55 mg of the title compound. 1H NMR (CDCl3, 200 MHz): δ=14.0 (s, 1H), 8.20-8.40 (m, 2H), 7.98 (d, 1H, J=0.8

Workup

customThe solvent was evaporated
customthe residue was purified by column chromatography (0-25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-faa6c20b1e4a47e986eafbbcd0caed58
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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