Glycine → HCID 24757162, compound

HRID 642320Notes

Reaction equation

HRID 642320 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[C:19]([Br:21])[CH:20]=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>[Br:21][C:19]1[CH:20]=[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:16]=[N:17][CH:18]=1

Participants

4

Reactant 2

HCID 750GlycineHCID 68427372HCID 68427372, compound

Product 1

HCID 24757162HCID 24757162, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 2-(5-bromo-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (49 mg, 0.13 mmol) and glycine (193 mg, 2.57 mmol) in 0.5 M sodium methoxide/methanol (4.9 mL) was refluxed for 36 h before it was cooled to room temperature and concentrated in vacuo. It was dissolved in water (15 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (2 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (13 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.34 (br s, 1H), 12.83 (br s, 1H), 9.46 (t, 1H), 9.30 (d, 1H), 8.91 (m, 2H), 8.73 (m, 1H), 4.02 (d, J=5.8 Hz, 2H); MS: (+) m/z 408.93, 410.87 (M+1, 79Br/81Br).

Workup

  1. temperaturewas refluxed for 36 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionIt was dissolved in water (15 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-f07f1517de034e92b67bf0161fc51c5d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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