4-Methylmorpholine → N-(2-aminophenyl)-5-(phenoxyacetyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide
Reaction equation
[O:1]([CH2:8][C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.CN1CCOCC1.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[NH:47][C:48]([C:50]1[S:51][C:52]2[CH2:53][NH:54][CH2:55][CH2:56][C:57]=2[N:58]=1)=[O:49]>CN(C=O)C>[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[NH:47][C:48]([C:50]1[S:51][C:52]2[CH2:53][N:54]([C:9](=[O:11])[CH2:8][O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:55][CH2:56][C:57]=2[N:58]=1)=[O:49]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To the solution of phenoxy acetic acid (1.0 mmol) in dry DMF (10 mL), were added 1-hydroxybenzotriazole (1.2 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (2 mmol) and N-methylmorpholine (2.0 mmol). Solution was cooled to 0° C. N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide obtained in step VIII of example I was then added and mixture was stirred at room temperature overnight. Reaction mixture was concentrated, diluted with water, extracted with dichloromethane, washed with brine solution, and dried over anhydrous Na2SO4. Concentrated and purified by column chromatograph to obtained the title compound.
Workup
- customReaction mixture
- concentrationwas concentrated
- additiondiluted with water
- extractionextracted with dichloromethane
- washwashed with brine solution
- dry with materialdried over anhydrous Na2SO4
- concentrationConcentrated
- custompurified by column chromatograph
Sources & evidence
- ORD record
- ord-b917ad543f854ab3afe745fe7d361d96
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440830B2
Reaction notes
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