Beta-Alanine → 3-[(4-Hydroxy-1-methyl-7 phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid

HRID 1481117

Reaction equation

HRID 1481117 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([CH3:23])[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][CH:18]=1)[CH:9]=2)=[O:4].[NH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].C[O-].[Na+].CO>>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:11][CH:12]=2)[C:7]([CH3:23])=[N:6][C:5]=1[C:3]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:4]

Participants

4

Reactant 3

HCID 239Beta-AlanineHCID 23694274Sodium methanolate methanolHCID 712448953-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester

Product 1

HCID 898128553-[(4-Hydroxy-1-methyl-7 phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acidYield 82.1%

Procedure

A mixture of 4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (120 mg, 0.39 mmol) and beta-alanine (242 mg, 2.72 mmol) in 0.5 M NaOMe/MeOH solution (4.5 mL, 2.25 mmol) was microwaved at 120° C. for 30 min. Reaction mixture was concentrated and dissolved in water (100 mL). It was acidified by 1 N HCl to pH=3-4. Gummy precipitate was collected by filtration and dissolved in EtOAc. It was dried over MgSO4, filtered and concentrated to provide the title compound 116 mg (0.32 mmol) in 81% yield. LC-MS ESI−: 365.16 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 30 min
  2. customReaction mixture
  3. concentrationwas concentrated
  4. dissolutiondissolved in water (100 mL)
  5. filtrationGummy precipitate was collected by filtration
  6. dissolutiondissolved in EtOAc
  7. dry with materialIt was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a8b543e6e47b4103b198a565651bca07
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Linked notes

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