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

HRID 1480984Notes

Reaction equation

HRID 1480984 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:24]#[N:25])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:10]=2)=[O:5])C.[C:26]([O:30][C:31](=[O:37])[C:32]([CH3:36])([CH3:35])[CH2:33][NH2:34])([CH3:29])([CH3:28])[CH3:27]>CCO>[C:26]([O:30][C:31](=[O:37])[C:32]([CH3:36])([CH3:35])[CH2:33][NH:34][C:4]([C:6]1[N:7]=[C:8]([C:24]#[N:25])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:10]=2)=[O:5])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 15430260Tert-butyl 3-amino-2,2-dimethylpropanoateHCID 898130801-Cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 898131463-{[1-Cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carbonyl]amino}-2,2-dimethyl-propionic acid tert-butyl esterYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester (19 mg) and 3-amino-2,2-dimethyl-propionic acid tert-butyl ester (25 mg) in EtOH (0.3 mL) was microwaved at 140° C. for 1 h. The mixture was cooled, concentrated and the residue was column purified to give the desired product (21 mg). LC MS ESI+: 463 (M+1)+.

Workup

  1. customwas microwaved at 140° C. for 1 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-f06ad71f8f6444d3b713df4dc82a3215
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…