Glycine → HCID 24757071, compound

HRID 642296Notes

Reaction equation

HRID 642296 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][C:18]([O:21][CH3:22])=[CH:17][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:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=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 68428789HCID 68428789, compound

Product 1

HCID 24757071HCID 24757071, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-(4-methoxy-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (76 mg, 0.23 mmol) and glycine (345 mg, 4.59 mmol) in 0.5 M sodium methoxide/methanol (8.7 mL) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. Water (20 mL) was added and the suspension was adjusted to pH=10 with 1N HCl (3 mL). The mixture was extracted with dichloromethane. And the remaining aqueous layer was acidified to pH=3 with 1N HCl (5 mL). The suspension was extracted with 2-isopropanol/chloroform (1:3, 50 mL). The organic layer was concentrated and dried in vacuo to give the title compound as a yellow solid (25 mg): 1H NMR (DMSO-d6, 200 MHz): δ=12.28 (s, 1H), 9.42 (t, 1H), 8.88 (s, 1H), 8.13 (d, J=8.8 Hz, 2H), 7.16 (d, J=8.8 Hz, 2H), 4.03 (d, J=5.6 Hz, 2H), 3.88 (s, 3H); MS: (+) m/z 359.94 (M+1), (−) m/z 357.92 (M−1).

Workup

  1. temperaturewas refluxed for 3 days before it
  2. concentrationconcentrated in vacuo
  3. additionWater (20 mL) was added
  4. extractionThe mixture was extracted with dichloromethane
  5. extractionThe suspension was extracted with 2-isopropanol/chloroform (1:3, 50 mL)
  6. concentrationThe organic layer was concentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-205abc1382e04389bc1f4890bd9381d7
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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