Tert-butyl 3-amino-2,2-dimethylpropanoate → 3-[(7-Benzyl-1-cyano-4-hydroxy-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid tert-butyl ester

HRID 1481209Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 7-Benzyl-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (20 mg, 0.06 mmole) and 3-amino-2,2-dimethyl-propionic acid tert-butyl ester (22 mg, 0.12 mmole) in anhydrous ethanol (0.6 ml) was stirred at 130° C. in a CEM microwave synthesizer for one hour before it was cooled to room temperature, concentrated and purified by flash column chromatography on silica gel with a gradient of dichloromethane and hexanes to give the title compound as a white solid (22 mg). LC-MS ESI+: 460 (M+1)+; ESI−: 458 (M−1)−.

Workup

temperaturewas cooled to room temperature
concentrationconcentrated
custompurified by flash column chromatography on silica gel with a gradient of dichloromethane and hexanes

Sources & evidence

ORD record: ord-9bbe7a910e574f74874f8495fe5f9f7e
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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