Glycine → HCID 24757416, compound

HRID 642369Notes

Reaction equation

HRID 642369 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]#[N:13])[C:9]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[S:16][C:8]=2[C:7]=1[OH:24])=[O:5])C.[NH2:25][CH2:26][C:27]([OH:29])=[O:28]>C[O-].[Na+].CO>[C:12]([C:10]1[C:9]2[N:14]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[S:16][C:8]=2[C:7]([OH:24])=[C:6]([C:4]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:5])[N:11]=1)#[N:13]

Participants

4

Reactant 2

HCID 750GlycineHCID 68426450HCID 68426450, compound

Product 1

HCID 24757416HCID 24757416, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-cyano-2-(4-fluoro-phenyl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (67 mg, 0.19 mmole) and glycine (875 mg, 11.66 mmole) in 0.5 M sodium methoxide/methanol (9.7 ml) was refluxed for 22 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (50 ml) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (12 ml). The suspension was extracted with ethyl acetate. The organic layer was washed with water and dried in vacuo to give the title compound as a yellow solid (59 mg). MS: (+) m/z 373.24 (M+1).

Workup

  1. temperaturewas refluxed for 22 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (50 ml)
  4. extractionextracted twice with dichloromethane
  5. extractionThe suspension was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-72daa60a23164bd7954f33e454c90ff4
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

Loading…