Glycine → HCID 24757415, compound

HRID 642367Notes

Reaction equation

HRID 642367 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)[C:9]2[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[S:22][C:8]=2[C:7]=1[OH:29])=[O:5])C.[NH2:30][CH2:31][C:32]([OH:34])=[O:33]>C[O-].[Na+].CO>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:9]3[N:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[S:22][C:8]=3[C:7]([OH:29])=[C:6]([C:4]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:5])[N:11]=2)=[CH:13][CH:14]=1)#[N:19]

Participants

4

Reactant 2

HCID 750GlycineHCID 68428007HCID 68428007, compound

Product 1

HCID 24757415HCID 24757415, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-(4-cyano-phenyl)-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (132 mg, 0.33 mmole) and glycine (2.46 g, 32.8 mmole) in 0.5 M sodium methoxide/methanol (49 ml) was refluxed for 16 h before it was cooled to room temperature and concentrated in vacuo. It was dissolved in water (100 ml) and extracted with dichloromethane (2×50 ml). The remaining aqueous solution was acidified to pH=2 with 0.1 N HCl (28 ml). The resulting precipitate was filtered, washed with water and dried to give the title compound as a white solid (76 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.56 (t, 1H), 8.91 (d, J=8.2 Hz, 2H), 8.19 (m, 2H), 8.00 (d, J=8.2 Hz, 2H), 7.64 (m, 3H), 4.07 (d, J=6.2 Hz, 2H); MS: (+) m/z 429.23 (M−1).

Workup

  1. temperaturewas refluxed for 16 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionIt was dissolved in water (100 ml)
  4. extractionextracted with dichloromethane (2×50 ml)
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-4502de938396417985749d868760f482
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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