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

HRID 1480970Notes

Reaction equation

HRID 1480970 reaction equation
C(O[C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=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]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=1)[CH:10]=2)=[O:5])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 15430260Tert-butyl 3-amino-2,2-dimethylpropanoateHCID 898129377-(4-Chloro-3-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 898130873-{[7-(4-Chloro-3-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acid tert-butyl esterYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(4-chloro-3-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester (45 mg) and 3-amino-2,2-dimethyl-propionic acid tert-butyl ester (65 mg) in EtOH (0.5 mL) was microwaved at 145° C. for 3 h. The mixture was cooled, concentrated and the residue was column purified to give the desired product (36 mg). LC MS ESI+: 489 (M+1)+.

Workup

  1. customwas microwaved at 145° C. for 3 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-252b75e5f457479d92d2a0e10fc5e42b
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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