Beta-Alanine → 3-{[4-Hydroxy-7-(pyridin-2-yloxy)-isoquinoline-3-carbonyl]amino}-propionic acid

HRID 1480979Notes

Reaction equation

HRID 1480979 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH:9]=2)=[O:4].[NH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27].C[O-].[Na+]>>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:4]

Participants

4

Reactant 3

HCID 239Beta-AlanineHCID 10942334Sodium MethoxideHCID 898129234-Hydroxy-7-(pyridin-2-yloxy)-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 898129183-{[4-Hydroxy-7-(pyridin-2-yloxy)-isoquinoline-3-carbonyl]amino}-propionic acidYield 76.9%

Procedure

A mixture of 4-hydroxy-7-(pyridin-2-yloxy)-isoquinoline-3-carboxylic acid methyl ester (24 mg), 3-amino-propionic acid (29 mg) and NaOMe (0.48 mL, 0.5 M solution in MeOH) was microwaved at 130° C. for 1 h; then cooled, concentrated, residue was dissolved in water, acidified with 2 M HCl; solids were collected via filtration, washed with water and air dried to give the desired product (22 mg). LC MS ESI: 354 (M+1)+.

Workup

  1. customwas microwaved at 130° C. for 1 h
  2. temperaturethen cooled
  3. concentrationconcentrated
  4. dissolutionresidue was dissolved in water
  5. filtrationsolids were collected via filtration
  6. washwashed with water and air
  7. customdried

Sources & evidence

ORD record
ord-38ad0edbad1f451f8813ee215113609d
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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