Piperidine → 3-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-4-methyl-5-oxo-6-(1-piperidyl)-4,5-dihydro-imidazo(1,5-a)quinazoline

HRID 2351319Notes

Reaction equation

HRID 2351319 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[N:10]=[CH:11][N:12]4[C:21]5[C:16](=[C:17](Cl)[CH:18]=[CH:19][CH:20]=5)[C:15](=[O:23])[N:14]([CH3:24])[C:13]=34)[N:5]=2)[CH2:3][CH2:2]1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CN(C)C=O>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[N:10]=[CH:11][N:12]4[C:21]5[C:16](=[C:17]([N:25]6[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]6)[CH:18]=[CH:19][CH:20]=5)[C:15](=[O:23])[N:14]([CH3:24])[C:13]=34)[N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 14460518HCID 14460518, compound

Product 1

HCID 144605323-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-4-methyl-5-oxo-6-(1-piperidyl)-4,5-dihydro-imidazo(1,5-a)quinazolineYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4-methyl-5-oxo-6-chloro-4,5-dihydro-imidazo(1,5-a)quinazoline (0.28 g, 0.8 mmol) was heated to 110° C. for 2 1/4 h in a mixture of 20 ml of dimethylformamide and 1 ml of piperidine. The reaction mixture was then evaporated in vacuo and the residue triturated with 5 ml of water, filtered off and dried to give 0.26 g (81%) 3- (5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4-methyl -5-oxo- 6-(1-piperidyl)-4,5-dihydro-imidazo(1,5-a)quinazoline, M.p. 185°-192° C..

Workup

  1. customThe reaction mixture was then evaporated in vacuo
  2. customthe residue triturated with 5 ml of water
  3. filtrationfiltered off
  4. customdried

Sources & evidence

ORD record
ord-0d3e16847c6c4f3d8359b52f744a2844
Source dataset
uspto-grants-1989_10
Patent number
US04873244

Reaction notes

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