Hydrochloric Acid → HCID 68428207, compound

HRID 642564Notes

Reaction equation

HRID 642564 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]([CH3:20])([CH3:19])[CH3:18])[S:16][C:8]=2[C:7]=1[OH:21])=[O:5])C.[NH2:22][CH2:23][C:24]([OH:26])=[O:25].Cl>C[O-].[Na+].CO.O>[C:17]([C:15]1[S:16][C:8]2[C:7]([OH:21])=[C:6]([C:4]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:5])[N:11]=[C:10]([C:12]#[N:13])[C:9]=2[N:14]=1)([CH3:18])([CH3:19])[CH3:20]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 750GlycineHCID 68428506HCID 68428506, compound

Product 1

HCID 68428207HCID 68428207, compoundYield 53.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A suspension of 2-tert-butyl-4-cyano-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (85 mg, 0.28 mmol) and glycine (188 mg, 2.5 mmol) in 4.4 mL of 0.5 N NaOMe in methanol was heated at reflux temperature for 25 h. The reaction mixture was diluted with water, acidified with 1 N HCl, and extracted with ethyl acetate. The organic fraction was concentrated to a residue and purified by reverse phase chromatography on a C-18 column, eluting the desired product with a gradient of 10-90% acetonitrile in water+0.1% formic acid. The lyophilized material fractions provided 50 mg of white solid. MS (ESI−): m/z 333.0 (M−1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 25 h
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic fraction was concentrated to a residue
  5. custompurified by reverse phase chromatography on a C-18 column
  6. washeluting the desired product with a gradient of 10-90% acetonitrile in water+0.1% formic acid

Sources & evidence

ORD record
ord-a9fed6bbc59a40d293d5950cd048a460
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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