Glycine → [(4-Cyano-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid

HRID 642337Notes

Reaction equation

HRID 642337 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]#[N:13])[C:9]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:16][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>[C:12]([C:10]1[C:9]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:16][C:8]=2[C:7]([OH:23])=[C:6]([C:4]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:5])[N:11]=1)#[N:13]

Participants

4

Reactant 2

HCID 750GlycineHCID 684277424-Cyano-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 24757246[(4-Cyano-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-cyano-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (39 mg, 0.12 mmole) and glycine (182 mg, 2.41 mmole) in 0.5 M sodium methoxide/methanol (4.6 ml) was refluxed for 28 hours before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (15 ml) and extracted twice with methyl tert-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (3.5 ml). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (34 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.73 (br s, 1H), 8.20 (m, 2H), 7.66 (m, 3H), 4.02 (d, J=6.2 Hz, 2H); MS: (−) m/z 352.82 (M−1).

Workup

  1. temperaturewas refluxed for 28 hours before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (15 ml)
  4. extractionextracted twice with methyl tert-butyl ether
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e53c2284a1ea4b3dabe4523c46728151
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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