Glycine → HCID 24780273, compound

HRID 409209Notes

Reaction equation

HRID 409209 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:21]#[N:22])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:23][CH2:24][C:25]([OH:27])=[O:26].C[O-].[Na+].CO>>[C:21]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:7])[N:9]=1)#[N:22]

Participants

5

Reactant 4

HCID 750GlycineHCID 887MethanolHCID 10942334Sodium MethoxideHCID 67110198HCID 67110198, compound

Product 1

HCID 24780273HCID 24780273, compoundYield 77.8%

Procedure

A mixture of 1-cyano-4-hydroxy-6-methoxy-isoquinoline-3-carboxylic acid butyl ester (104 mg, 0.35 mmol), glycine (523 mg, 6.97 mmol), and a 0.5 M solution of sodium methoxide in methanol (13.2 mL, 6.6 mmol) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (30 mL) and the solution was extracted with methyl tert-butyl ether (2×25 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl (10 mL). The resulting white precipitate was collected by filtration, washed with water and dried in vacuo to give the title compound as a white solid (82 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.53 (t, 1H), 8.10 (d, J=9.0 Hz, 1H), 7.57 (m, 2H), 4.02 (d, J=6.2 Hz, 2H), 3.98 (s, 3H); MS: (+) m/z 302.00 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. extractionthe solution was extracted with methyl tert-butyl ether (2×25 mL)
  4. filtrationThe resulting white precipitate was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ab70cbae4cda412190810702e8fd273c
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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