Glycine → HCID 24780837, compound

HRID 409320Notes

Reaction equation

HRID 409320 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-d503a302a0734a1394b7be3d7ab2a809
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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