Glycine → HCID 24780837, compound

HRID 706252Notes

Reaction equation

HRID 706252 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:20]#[N:21])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([Cl:19])=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:22][CH2:23][C:24]([OH:26])=[O:25]>C[O-].[Na+].CO>[Cl:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[C:10]([C:20]#[N:21])=[N:9][C:8]([C:6]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:7])=[C:17]2[OH:18]

Participants

4

Reactant 2

HCID 750GlycineHCID 67110529HCID 67110529, compound

Product 1

HCID 24780837HCID 24780837, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 6-chloro-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (99 mg, 0.33 mmol) and glycine (1.84 g, 24.49 mmol) in 0.5 M sodium methoxide/methanol (32.6 mL) was refluxed for twenty-one hours before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (40 mL) and the solution washed with dichloromethane (3×50 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl. The suspension was extracted with ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a white solid (84 mg): MS: (+) m/z 306.27 (M+1); (−) m/z 304.26 (M−1).

Workup

  1. temperaturewas refluxed for twenty-one hours before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (40 mL)
  4. washthe solution washed with dichloromethane (3×50 mL)
  5. extractionThe suspension was extracted with ethyl acetate (50 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8f4785fcf0a4c36a3b48389376907cd
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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