Tert-butyl 3-amino-2,2-dimethylpropanoate → 3-{[1-Cyano-4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carbonyl]amino}-2,2-dimethyl-propionic acid tert-butyl ester

HRID 1480959Notes

Reaction equation

HRID 1480959 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][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[C:27]([O:31][C:32](=[O:38])[C:33]([CH3:37])([CH3:36])[CH2:34][NH2:35])([CH3:30])([CH3:29])[CH3:28]>CO>[C:27]([O:31][C:32](=[O:38])[C:33]([CH3:37])([CH3:36])[CH2:34][NH:35][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:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[CH:9]=2)=[O:4])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 15430260Tert-butyl 3-amino-2,2-dimethylpropanoateHCID 898132171-Cyano-4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 898128363-{[1-Cyano-4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carbonyl]amino}-2,2-dimethyl-propionic acid tert-butyl esterYield 65.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-cyano-4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester (91 mg) and 3-amino-2,2-dimethyl-propionic acid tert-butyl ester (90 mg) in MeOH (3 mL) was heated at 100° C. in an oil bath for 48 h. The mixture was cooled, concentrated and the residue was column purified to give the desired product (84 mg). LC MS ESI+: 492 (M+1)+.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. custompurified

Sources & evidence

ORD record
ord-3e6735775049448bbc245a17dcaa7091
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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