Ethyl 3-amino-2,2-dimethylpropanoate → HCID 89812939, compound

HRID 1481174Notes

Reaction equation

HRID 1481174 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:27]#[N:28])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH:10]=2)=[O:5])C.[CH2:29]([O:31][C:32](=[O:38])[C:33]([CH3:37])([CH3:36])[CH2:34][NH2:35])[CH3:30]>C(O)C>[CH2:29]([O:31][C:32](=[O:38])[C:33]([CH3:37])([CH3:36])[CH2:34][NH:35][C:4]([C:6]1[N:7]=[C:8]([C:27]#[N:28])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH:10]=2)=[O:5])[CH3:30]

Participants

4

Reactant 2

HCID 421529Ethyl 3-amino-2,2-dimethylpropanoateHCID 89813042HCID 89813042, compound

Product 1

HCID 89812939HCID 89812939, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Cyano-4-hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carboxylic acid ethyl ester (40 mg, 0.106 mmol) was dissolved/suspended in ethanol (3 mL) and 3-Amino-2,2-dimethyl-propionic acid ethyl ester (46 mg, 0.318 mmol) was added via syringe. The reaction was brought to reflux and maintained for 50 h. The reaction was cooled, concentrated and purified by medium pressure liquid chromatography (15 to 60% ethyl acetate in hexanes) to give the product as a white solid which was used immediately in the following reaction.

Workup

  1. temperatureto reflux
  2. temperaturemaintained for 50 h
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. custompurified by medium pressure liquid chromatography (15 to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-971fa42ec53047e3b80c3e413d835417
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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