Sodium Carbonate → Ethyl 4-Methyl-2-(morpholin-4-ylmethyl)-7-oxo-4,7-dihydro[1,3]thiazolo[5,4-b]pyridine-6-carboxylate

HRID 1070628Notes

Reaction equation

HRID 1070628 reaction equation
CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:20][N:21]([CH:34]=[C:35]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:36](OCC)=[O:37])[C:22]1[S:26][C:25]([CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[N:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:20][N:21]1[CH:34]=[C:35]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:36](=[O:37])[C:23]2[N:24]=[C:25]([CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[S:26][C:22]1=2

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 22397177Diethyl 2-((Methyl(2-(morpholin-4-ylmethyl)-1,3-thiazol-5-yl)amino)methylene)-malonateHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 22397170Ethyl 4-Methyl-2-(morpholin-4-ylmethyl)-7-oxo-4,7-dihydro[1,3]thiazolo[5,4-b]pyridine-6-carboxylateYield 28%

Conditions

Temperature
110 °C

Procedure

A mixture of Eaton's Reagent (1.5 mL) and diethyl 2-((methyl(2-(morpholin-4-yl-methyl)-1,3-thiazol-5-yl)amino)methylene)malonate (Preparation 29, 452 mg) is heated to 110° C. for 20 min. with a stream of nitrogen over the reaction. The mixture is cooled to ambient temperature and transferred to a cooled beaker. The solution is diluted with ice chips and neutralized by dropping Na2CO3 into the solution. The mixture is then extracted with CH2Cl2 (3×50 mL), the organic layer dried (MgSO4), and the solvent is removed. The residue is purified by column chromatography (eluent 5% MeOH/CH2Cl2) to afford 111 mg (28%) of the title compound as a brown solid. Physical characteristics: 1H NMR (CDCl3) δ1.39, 2.67, 3.77, 3.89, 3.90, 4.38, 8.25; IR (diffuse reflectance) 1726, 1716, 1679, 1632, 1614, 1609, 1586, 1507, 1330, 1300, 1236, 1194, 1113, 863, 801 cm−1. Anal. Found (C15H19N3O4S.0.75 H2O): C, 51.34; H, 5.94; N, 11.88.

Workup

  1. temperatureThe mixture is cooled to ambient temperature
  2. additionThe solution is diluted with ice chips
  3. extractionThe mixture is then extracted with CH2Cl2 (3×50 mL)
  4. dry with materialthe organic layer dried (MgSO4)
  5. customthe solvent is removed
  6. customThe residue is purified by column chromatography (eluent 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a3008776563249d880305859f0931331
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

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