Glycine → HCID 24757243, compound

HRID 642329Notes

Reaction equation

HRID 642329 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([CH3:12])[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[S:15][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>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[S:15][C:8]3[C:7]([OH:23])=[C:6]([C:4]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:5])[N:11]=[C:10]([CH3:12])[C:9]=3[N:13]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 750GlycineHCID 68427942HCID 68427942, compound

Product 1

HCID 24757243HCID 24757243, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 2-(4-fluoro-phenyl)-7-hydroxy-4-methyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (70 mg, 0.21 mmol) and glycine (317 mg, 4.23 mmol) in 0.5 M sodium methoxide/methanol (8 mL) was refluxed for four days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (25 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (6 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (62 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.01 (br s, 1H), 9.22 (br s, 1H), 8.20 (m, 2H), 7.40 (m, 2H), 4.03 (d, J=5.9 Hz, 2H), 2.86 (s, 3H); MS: (+) m/z 361.87 (M+1).

Workup

  1. temperaturewas refluxed for four days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (25 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-334d7629137c43a8984a6ac74087f279
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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