Glycine → HCID 135745068, compound

HRID 642348Notes

Reaction equation

HRID 642348 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[C:9]2[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:19][C:8]=2[C:7]=1[OH:26])=[O:5])C.[NH2:27][CH2:28][C:29]([OH:31])=[O:30]>C[O-].[Na+].CO>[OH:26][C:7]1[C:8]2[S:19][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:17][C:9]=2[C:10]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[N:11][C:6]=1[C:4]([NH:27][CH2:28][C:29]([OH:31])=[O:30])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 136389262HCID 136389262, compound

Product 1

HCID 135745068HCID 135745068, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-phenyl-4-thiazol-2-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (25 mg, 0.06 mmole) and glycine (96 mg, 1.28 mmole) in 0.5 M sodium methoxide/methanol (2.4 ml) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. It was dissolved in water (25 ml) and extracted with dichloromethane (2×50 ml). The remaining aqueous solution was acidified to pH=2 with 0.1 N HCl (1.8 ml). The resulting suspension was extracted with isopropanol/chloroform (50 ml, 1:3) dichloromethane, washed with brine, dried over sodium sulfate and concentrated in vacuo to give a yellow solid which was further purified by MPLC on a C18 column with a gradient of formic acid, acetonitrile and water to give the title compound as a yellow solid (8 mg). 1H NMR (DMSO-d6, 200 MHz): δ=8.21 (m, 2H), 8.01 (m, 1H), 7.89 (m, 1H), 7.63 (m, 3H), 6.51 (m, 1H), 4.10 (d, J=5.4 Hz, 2H); MS: (+) m/z 413.22 (M+1).

Workup

  1. temperaturewas refluxed for 3 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionIt was dissolved in water (25 ml)
  4. extractionextracted with dichloromethane (2×50 ml)
  5. extractionThe resulting suspension was extracted with isopropanol/chloroform (50 ml, 1:3) dichloromethane
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a yellow solid which
  10. customwas further purified by MPLC on a C18 column with a gradient of formic acid, acetonitrile and water

Sources & evidence

ORD record
ord-daefc0696f5b4b82bbfeba23de377e4f
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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