Glycine → HCID 24757417, compound

HRID 642372Notes

Reaction equation

HRID 642372 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][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[S:16][C:8]=2[C:7]=1[OH:25])=[O:5])C.[NH2:26][CH2:27][C:28]([OH:30])=[O:29]>C[O-].[Na+].CO>[C:12]([C:10]1[C:9]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[S:16][C:8]=2[C:7]([OH:25])=[C:6]([C:4]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:5])[N:11]=1)#[N:13]

Participants

4

Reactant 2

HCID 750GlycineHCID 68428589HCID 68428589, compound

Product 1

HCID 24757417HCID 24757417, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-cyano-7-hydroxy-2-(3-methoxy-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (34 mg, 0.10 mmole) and glycine (538 mg, 7.16 mmole) in 0.5 M sodium methoxide/methanol (9.5 ml) was refluxed for 21 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (25 ml) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (7 ml). The suspension was extracted with ethyl acetate and dichloromethane. The organic layers were combined and washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (34 mg). MS: (+) m/z 385.17 (M+1), MS: (−) m/z 383.13 (M−1).

Workup

  1. temperaturewas refluxed for 21 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (25 ml)
  4. extractionextracted twice with dichloromethane
  5. extractionThe suspension was extracted with ethyl acetate and dichloromethane
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-499d5aa8f74a4f92bcc3657d24984564
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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