Glycine → {[7-Hydroxy-4-(4-morpholin-4-yl-phenyl)-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl]-amino}-acetic acid

HRID 642365Notes

Reaction equation

HRID 642365 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[C:9]2[S:24][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:26][C:8]=2[C:7]=1[OH:33])=[O:5])C.[NH2:34][CH2:35][C:36]([OH:38])=[O:37]>C[O-].[Na+].CO>[OH:33][C:7]1[C:8]2[N:26]=[C:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[S:24][C:9]=2[C:10]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:14][CH:13]=2)=[N:11][C:6]=1[C:4]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 684263857-Hydroxy-4-(4-morpholin-4-yl-phenyl)-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 24757414{[7-Hydroxy-4-(4-morpholin-4-yl-phenyl)-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl]-amino}-acetic acidYield 74.7%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-Hydroxy-4-(4-morpholin-4-yl-phenyl)-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (56 mg, 0.12 mmole) and glycine (182 mg, 2.43 mmole) in 0.5 M sodium methoxide/methanol (4.4 ml) was refluxed for 5 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (120 ml) and extracted with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (5 ml). The resulting suspension was extracted with ethyl acetate, washed with brine and dried in vacuo to give the title compound as a yellow solid (44 mg). 1H NMR (DMSO-d6, 200 MHz): δ=13.1 (br s, 1H), 9.37 (t, 1H), 8.15 (m, 2H), 8.04 (m, 2H), 7.62 (m, 3H), 7.10 (m, 2H), 4.06 (d, 2H, J=5.8 Hz), 3.77 (m, 4H); MS: (+) m/z 491.22 (M+1).

Workup

  1. temperaturewas refluxed for 5 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (120 ml)
  4. extractionextracted with dichloromethane
  5. extractionThe resulting suspension was extracted with ethyl acetate
  6. washwashed with brine
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c228c32e28464d64be953f006c92ecb2
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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