Beta-Alanine → HCID 71736438, compound

HRID 1481122Notes

Reaction equation

HRID 1481122 reaction equation
C(O[C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30]>C[O-].[Na+].CO>[OH:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=2)[CH:10]=[N:9][C:8]=1[C:6]([NH:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:7]

Participants

4

Reactant 2

HCID 239Beta-AlanineHCID 66712741HCID 66712741, compound

Product 1

HCID 71736438HCID 71736438, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-hydroxy-6-phenoxy-isoquinoline-3-carboxylic acid butyl ester (200 mg, 0.59 mmol) (prepared according to U.S. Pat. No. 7,629,357) and beta-alanine (792 mg, 8.9 mmol) in 0.5 M NaOMe/MeOH solution was refluxed overnight. Reaction mixture was concentrated and residue was dissolved in water (150 mL). It was cidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried in vacuo to provide the title compound 196 mg (0.56 mmol) in 94% yield. LC-MS ESI−: 351.05 (M−1)−.

Workup

  1. customprepared
  2. customReaction mixture
  3. concentrationwas concentrated
  4. dissolutionresidue was dissolved in water (150 mL)
  5. customPrecipitate was collected
  6. washrinsed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a883ede827b446938bc4c6a2f8ae0964
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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