Potassium Iodide → 3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy-2-methylpyrido[1,2-a]pyrimidin-4-one
Reaction equation
Cl.Cl[CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:8]2=[N:7][C:6]=1[CH3:17].Cl.[F:19][C:20]1[CH:34]=[CH:33][C:23]2[C:24]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[N:25][O:26][C:22]=2[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(#N)C>[F:19][C:20]1[CH:34]=[CH:33][C:23]2[C:24]([CH:27]3[CH2:28][CH2:29][N:30]([CH2:3][CH2:4][C:5]4[C:10](=[O:11])[N:9]5[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:8]5=[N:7][C:6]=4[CH3:17])[CH2:31][CH2:32]3)=[N:25][O:26][C:22]=2[CH:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 82.5 °C
Procedure
A mixture of 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride (formula-5) (11.1 grams), 6-fluoro-3-(4-piperidinyl)-1,2-benzoisoxazole mono hydrochloride (formula-6) (10 grams), sodium carbonate (7.5 grams), potassium iodide (0.64 grams) in acetonitrile (100 ml) was heated to 80-85° C. The reaction mixture was refluxed for 17 hrs under nitrogen. Then it was cooled to −10° C. and stirred for 30 min. The solid obtained was filtered and washed with chilled acetonitrile. The solid was taken in water and treated with sodiumhydrosulphite (hydrose) (2.0 grams). The solid was filtered and washed with water and dried at 50° C. to provide the title compound.
Workup
- temperatureThe reaction mixture was refluxed for 17 hrs under nitrogen
- temperatureThen it was cooled to −10° C.
- customThe solid obtained
- filtrationwas filtered
- washwashed with chilled acetonitrile
- additiontreated with sodiumhydrosulphite (hydrose) (2.0 grams)
- filtrationThe solid was filtered
- washwashed with water
- customdried at 50° C.
Sources & evidence
- ORD record
- ord-c5ea3a6f858943d5b13ac4b15dff9dcd
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481729B2
Reaction notes
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