Tert-butyl 3-amino-2,2-dimethylpropanoate → 3-{[7-(2-Chloro-5-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acid tert-butyl ester

HRID 1480994Notes

Reaction equation

HRID 1480994 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:26]#[N:27])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[Cl:25])[CH:10]=2)=[O:5])C.[C:28]([O:32][C:33](=[O:39])[C:34]([CH3:38])([CH3:37])[CH2:35][NH2:36])([CH3:31])([CH3:30])[CH3:29]>CCO>[C:28]([O:32][C:33](=[O:39])[C:34]([CH3:38])([CH3:37])[CH2:35][NH:36][C:4]([C:6]1[N:7]=[C:8]([C:26]#[N:27])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[Cl:25])[CH:10]=2)=[O:5])([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 15430260Tert-butyl 3-amino-2,2-dimethylpropanoateHCID 898130057-(2-Chloro-5-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 898130243-{[7-(2-Chloro-5-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acid tert-butyl esterYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(2-chloro-5-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester (15 mg) and 3-amino-2,2-dimethyl-propionic acid tert-butyl ester (19 mg) in EtOH (0.7 mL) was microwaved at 150° C. for 2 h. The mixture was cooled, concentrated and the residue was column purified to give the desired product (19 mg). LC MS ESI+: 514 (M+1)+.

Workup

  1. customwas microwaved at 150° C. for 2 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-610e7a626d6441a195a9b43b675fcf54
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…