Glycine → {[1-Cyano-4-hydroxy-6-(4-propoxy-phenoxy)-isoquinoline-3-carbonyl]-amino}-acetic acid

HRID 706206Notes

Reaction equation

HRID 706206 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:30]#[N:31])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH3:29])=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:32][CH2:33][C:34]([OH:36])=[O:35].C[O-].[Na+].CO>>[C:30]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH3:29])=[CH:24][CH:25]=3)=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:32][CH2:33][C:34]([OH:36])=[O:35])=[O:7])[N:9]=1)#[N:31]

Participants

4

Reactant 3

HCID 750GlycineHCID 23694274Sodium methanolate methanolHCID 671102651-Cyano-4-hydroxy-6-(4-propoxy-phenoxy)-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 24780549{[1-Cyano-4-hydroxy-6-(4-propoxy-phenoxy)-isoquinoline-3-carbonyl]-amino}-acetic acidYield 117.5%

Procedure

A mixture of 1-cyano-4-hydroxy-6-(4-propoxy-phenoxy)-isoquinoline-3-carboxylic acid butyl ester (200 mg, 0.422 mmol), glycine (633 mg, 8.43 mmol) and NaOMe/MeOH solution (12.7 mL, 6.33 mmol) was refluxed overnight. Then the mixture was concentrated in vacuo and the residue was dissolved in water. The solution was acidified with 2 M HCl to pH=3-4. The resulting precipitate was collected by filtration, washed with water, and freeze-dried to give the title compound as a powder (209 mg); ESI MS (m/z): 422 (M+H)+.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThen the mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customfreeze-dried

Sources & evidence

ORD record
ord-bf1dc93cc02f4c86b4fd1734de32cbf4
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

Loading…