Morpholine → 4-{[2-(6-Chloropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]carbonyl}morpholine
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([O:16]CC)=O)=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:16])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of ethyl 2-(6-chloropyridin-3-yl)-4-methyl-1,3-thiazole-5-carboxylate i98 (0.47 g, 1 eq, 1.84 mmol), morpholine (0.19 g, 1.2 eq, 2.21 mmol) and triethylamine (0.5 ml, 2 eq, 3.68 mmol) in dichloromethane (15 ml) is cooled to 0° C. N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.39 g, 1.1 eq, 2.02 mmol) and 1-hydroxybenzotriazole (0.05 g, 0.2 eq, 0.37 mmol) are then added to the solution and the mixture is stirred 24 h at room temperature. The mixture is then washed with water and a saturated solution of aqueous ammonium chloride. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum to give 0.53 g of 4-{[2-(6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]carbonyl}morpholine i99.
Workup
- washThe mixture is then washed with water
- dry with materialThe organic layer is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-067f455cf5b04987815cd92a1c7f284b
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790720B2
Reaction notes
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