Glycine → HCID 24757070, compound

HRID 642293Notes

Reaction equation

HRID 642293 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])C.[NH2:23][CH2:24][C:25]([OH:27])=[O:26]>C[O-].[Na+].CO>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[S:14][C:8]3[C:7]([OH:22])=[C:6]([C:4]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:5])[N:11]=[CH:10][C:9]=3[N:12]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 750GlycineHCID 68426366HCID 68426366, compound

Product 1

HCID 24757070HCID 24757070, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 2-(4-chloro-phenyl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (58 mg, 0.17 mmol) and glycine (259 mg, 3.45 mmol) in 0.5 M sodium methoxide/methanol (6.6 mL) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. Water (20 mL) was added and the mixture was extracted with dichloromethane. The remaining aqueous layer was acidified to pH=2 with 1N HCl. The suspension was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (11 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.44 (br s, 1H), 8.90 (s, 1H), 8.16 (d, J=8.6 Hz, 2H), 7.66 (d, J=8.6 Hz, 2H), 4.02 (d, 2H); MS: (+) m/z 364.0 (M+1)

Workup

  1. temperaturewas refluxed for three days before it
  2. concentrationconcentrated in vacuo
  3. additionWater (20 mL) was added
  4. extractionthe mixture was extracted with dichloromethane
  5. extractionThe suspension was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ed675e92f73495a925432e5846d44a0
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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