Diisopropylethylamine → 3-{2-[4-(6-Fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-2-methyl-7,8-dihydro-4H-pyrido[1,2-a]pyrimidine-4,9(6H)-dione

HRID 448541Notes

Reaction equation

HRID 448541 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.Cl[CH2:18][CH2:19][C:20]1[C:25](=[O:26])[N:24]2[CH2:27][CH2:28][CH2:29][C:30](=[O:31])[C:23]2=[N:22][C:21]=1[CH3:32].C(N(C(C)C)CC)(C)C>CO>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:18][CH2:19][C:20]4[C:25](=[O:26])[N:24]5[CH2:27][CH2:28][CH2:29][C:30](=[O:31])[C:23]5=[N:22][C:21]=4[CH3:32])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 44602516HCID 44602516, compound

Product 1

HCID 446083593-{2-[4-(6-Fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-2-methyl-7,8-dihydro-4H-pyrido[1,2-a]pyrimidine-4,9(6H)-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
26 °C

Procedure

To the solution of 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole (formula-8) (0.62 grams) taken in methanol added 3-(2-chloroethyl)-9-oxo-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (formula-9) (0.94 grams), diisopropyl ethyl amine (0.75 grams) and refluxed the reaction for 23 hrs. Cooled the reaction mixture to 26° C. and stirred for 15 minutes. Filtered the precipitated solid. Washed the solid with chilled methanol and dried. Separated the compound with column chromatography using chloroform/methanol as an eluent.

Workup

  1. temperaturerefluxed
  2. customthe reaction for 23 hrs
  3. filtrationFiltered the precipitated solid
  4. washWashed the solid with chilled methanol
  5. customdried
  6. customSeparated the compound with column chromatography

Sources & evidence

ORD record
ord-94502c24d614460883a677b03f9f20e2
Source dataset
uspto-grants-2013_07
Patent number
US08481729B2

Reaction notes

Loading…