Glycine → HCID 24757163, compound

HRID 642322Notes

Reaction equation

HRID 642322 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]=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:21])=[O:5])C.[NH2:22][CH2:23][C:24]([OH:26])=[O:25]>C[O-].[Na+].CO>[OH:21][C:7]1[C:8]2[S:14][C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[N:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 68427750HCID 68427750, compound

Product 1

HCID 24757163HCID 24757163, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-pyridin-3-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (27 mg, 0.09 mmol) and glycine (169 mg, 1.80 mmol) in 0.5 M sodium methoxide/methanol (4.5 mL) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. It was dissolved in water (15 mL) and extracted twice with methyl t-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (3.3 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (17 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.56 (br s, 1H), 9.34 (s, 1H), 8.94 (s, 1H), 8.80 (d, 1H), 8.53 (m, 1H), 7.66 (m, 1H), 4.03 (d, J=5.8 Hz, 2H); MS: (+) m/z 331.00 (M+1).

Workup

  1. temperaturewas refluxed for 3 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionIt was dissolved in water (15 mL)
  4. extractionextracted twice with methyl t-butyl ether
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-95c518e7aee8477cbc84365b9f0e178c
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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