Glycine → HCID 24757329, compound

HRID 642344Notes

Reaction equation

HRID 642344 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=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]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=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 68428390HCID 68428390, compound

Product 1

HCID 24757329HCID 24757329, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-(3-methoxy-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (129 mg, 0.39 mmole) and glycine (588 mg, 7.83 mmole) in 0.5 M sodium methoxide/methanol (14.8 ml) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. It was dissolved in water (50 ml) and extracted twice with methyl t-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (9 ml). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (122 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.48 (br s, 1H), 8.89 (s, 1H), 7.69 (m, 2H), 7.51 (m, 1H), 7.22 (m, 1H). 4.02 (d, J=6.2 Hz, 2H), 3.86 (s, 3H); MS: (+) m/z 359.90 (M+1); (−) m/z 357.92 (M−1).

Workup

  1. temperaturewas refluxed for 3 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionIt was dissolved in water (50 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-f62c2784fdfc48d5a2544ebe57d664b6
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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