Glycine → HCID 24757072, compound

HRID 642300Notes

Reaction equation

HRID 642300 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]([F: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>[F: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 68428542HCID 68428542, compound

Product 1

HCID 24757072HCID 24757072, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(4-fluoro-phenyl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (81 mg, 0.25 mmol) and glycine (190 mg, 5.07 mmol) in 0.5 M sodium methoxide/methanol (4.0 mL) was heated at 120° C. using a CEM microwave reactor for 1H before it was cooled to room temperature and concentrated in vacuo. It was dissolved in water (50 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (3 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a brown solid (66 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.28 (br s, 1H), 9.44 (br s, 1H), 8.91 (s, 1H), 8.21 (m, 2H), 7.45 (m, 2H), 4.03 (d, J=6.2 Hz, 2H); MS: (+) m/z 348.00 (M+1).

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionIt was dissolved in water (50 mL)
  4. extractionextracted twice with dichloromethane
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-42e1385471904285a0fea0cbae4ef571
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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