Glycine → {[7-Hydroxy-2-(4-trifluoromethyl-phenyl)-thiazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

HRID 642289Notes

Reaction equation

HRID 642289 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]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[S:14][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>[OH:25][C:7]1[C:8]2[S:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][CH:16]=3)=[N:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 684264227-Hydroxy-2-(4-trifluoromethyl-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 68426552{[7-Hydroxy-2-(4-trifluoromethyl-phenyl)-thiazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acidYield 77.8%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-(4-trifluoromethyl-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (40 mg, 0.11 mmol) and glycine (162 mg, 2.16 mmol) in 0.5 M sodium methoxide/methanol (4.1 mL) was refluxed for four days before it was cooled to room temperature and concentrated in vacuo. Water (20 mL) and 1N HCl (1.5 mL) was added and the mixture was extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (1.5 mL). 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 (34 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.48 (br s, 1H), 8.94 (s, 1H), 8.35 (d, 2H), 7.96 (d, 2H), 4.03 (d, J=5.8 Hz, 2H); MS: (+) m/z 329.9 (M+1)

Workup

  1. temperaturewas refluxed for four days before it
  2. concentrationconcentrated in vacuo
  3. additionWater (20 mL) and 1N HCl (1.5 mL) was added
  4. extractionthe mixture was extracted twice 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-418b84ef259b44dca9574f0a0e4c88c8
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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