Glycine → HCID 24757160, compound

HRID 642314Notes

Reaction equation

HRID 642314 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])C.[NH2:23][CH2:24][C:25]([OH:27])=[O:26]>C[O-].[Na+].CO>[OH:22][C:7]1[C:8]2[S:14][C:13]([NH:15][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:23][CH2:24][C:25]([OH:27])=[O:26])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 86617355HCID 86617355, compound

Product 1

HCID 24757160HCID 24757160, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-phenylamino-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (39 mg, 0.12 mmol) and glycine (186 mg, 2.48 mmol) in 0.5 M sodium methoxide/methanol (4.7 mL) was refluxed for 22 h 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 (3.5 mL). The suspension was extracted with ethyl acetate (2×30 mL) and chloroform/isopropanol (3:1, 40 mL). The organic layer was combined and dried in vacuo to give the title compound as a brown solid (35 mg): 1H NMR (DMSO-d6, 200 MHz): δ=12.99 (br s, 1H), 11.00 (s, 1H), 9.25 (t, 1H), 8.47 (s, 1H), 7.77 (m, 2H), 7.39 (t, 2H), 7.09 (t, 1H), 4.00 (d, J=6.3 Hz, 2H); MS: (+) m/z 345.07 (M+1).

Workup

  1. temperaturewas refluxed for 22 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionIt was dissolved in water (20 mL)
  4. extractionextracted twice with dichloromethane
  5. extractionThe suspension was extracted with ethyl acetate (2×30 mL) and chloroform/isopropanol (3:1, 40 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-facf8dd2cf6e45669250f2e0191662cc
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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