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

HRID 1480974Notes

Reaction equation

HRID 1480974 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:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:10]=2)=[O:5])C.[NH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].C[O-].[Na+]>>[OH:16][C:15]1[C:14]2[C:9](=[CH:10][C:11]([O:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7][C:6]=1[C:4]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:5]

Participants

4

Reactant 3

HCID 239Beta-AlanineHCID 10942334Sodium MethoxideHCID 898130784-Hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 898130233-{[4-Hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carbonyl]amino}-propionic acidYield 84.4%

Procedure

A mixture of 4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester (26 mg), 3-amino-propionic acid (30 mg) and NaOMe (0.50 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 (25 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-df575c52f6f949f2b2449ebb52804576
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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