Glycine → HCID 24757159, compound

HRID 642310Notes

Reaction equation

HRID 642310 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([N:15]([CH3:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:14][C:8]=2[C:7]=1[OH:23])=[O:5])C.[NH2:24][CH2:25][C:26]([OH:28])=[O:27]>C[O-].[Na+].CO>[OH:23][C:7]1[C:8]2[S:14][C:13]([N:15]([CH3:22])[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 68427186HCID 68427186, compound

Product 1

HCID 24757159HCID 24757159, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-(methyl-phenyl-amino)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (87 mg, 0.26 mmol) and glycine (399 mg, 5.31 mmol) in 0.5 M sodium methoxide/methanol (10.1 mL) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. It was dissolved in water (20 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (6.5 mL). The precipitate was filtered, washed with water and dried under vacuo to give the title compound as a white solid (77 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.18 (br s, 1H), 8.37 (s, 1H), 7.57 (m, 5H), 3.95 (d, J=6.2 Hz, 2H), 3.61 (s, 3H); MS: (+) m/z 359.0 (M+1).

Workup

  1. temperaturewas refluxed for three days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionIt was dissolved in water (20 mL)
  4. extractionextracted twice with dichloromethane
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried under vacuo

Sources & evidence

ORD record
ord-6779fb88a34c411d8dd0368702fc42ae
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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