Beta-Alanine → 3-{[4-Hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carbonyl]amino}-propionic acid

HRID 1481127Notes

Reaction equation

HRID 1481127 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]([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.[CH2:27]([C:30]([OH:32])=[O:31])[CH2:28][NH2:29].C[O-].[Na+].CO>>[OH:16][C:15]1[C:14]2[C:9](=[CH:10][C:11]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:19])=[CH:12][CH:13]=2)[CH:8]=[N:7][C:6]=1[C:4]([NH:29][CH2:28][CH2:27][C:30]([OH:32])=[O:31])=[O:5]

Participants

5

Reactant 4

HCID 239Beta-AlanineHCID 887MethanolHCID 10942334Sodium MethoxideHCID 898131284-Hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 898129013-{[4-Hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carbonyl]amino}-propionic acidYield 57%

Procedure

4-Hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carboxylic acid ethyl ester (75 mg, 0.2135 mmol) and B-alanine (191 mg, 2.135 mmol) were combined in a dry flask. 0.5M sodium methoxide in methanol (4.2 mL, 2.135 mmol) was added with stirring and the solution brought to reflux and held for 24 h. The mixture was cooled, concentrated in vacuo and the residue dissolved in water. The solution was acidified to pH 3 with 1M hydrochloric acid and the precipitate isolated by filtration. The crude product was purified by trituration with a minimal volume of methanol to provide the title compound in 57% yield. MS ESI(+) m/e: 395.1345 (M+1).

Workup

  1. temperatureto reflux
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionthe residue dissolved in water
  5. customthe precipitate isolated by filtration
  6. customThe crude product was purified by trituration with a minimal volume of methanol

Sources & evidence

ORD record
ord-e603a21c5ed64bd48c4e1aeaf20b6289
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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