HCID 18953450, compound → HCID 18953469, compound

HRID 1491609Notes

Reaction equation

HRID 1491609 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH3:18])[N:3]=1.[CH:19]1([C:22]2[N:26]=[C:25]([CH2:27][N+:28]#[C-:29])[O:24][N:23]=2)[CH2:21][CH2:20]1.CC(C)([O-])C.[K+]>CN(C)C=O>[CH:19]1([C:22]2[N:26]=[C:25]([C:27]3[N:28]=[CH:29][N:3]4[C:4]5[C:9](=[C:8]([CH3:18])[CH:7]=[CH:6][CH:5]=5)[C:10]([N:12]5[CH2:17][CH2:16][O:15][CH2:14][CH2:13]5)=[N:11][C:2]=34)[O:24][N:23]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 18953450HCID 18953450, compoundHCID 229129243-Cyclopropyl-5-(isocyanomethyl)-1,2,4-oxadiazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 18953469HCID 18953469, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-chloro-5-methyl-4-morpholino-quinazoline (1.68 g, 6.4 mmol) and 3-cyclopropyl-5-isocyanomethyl-1,2,4-oxadiazole (1.9 g) in 15 ml of dry dimethylformamide was cooled to 0° C. Solid potassium tert-butoxide (1.4 g, 12.5 mmol) was added gradually during 5 min. to the stirred mixture, the temperature being kept below 10° C. The mixture was stirred at ambient temperature for two hors, and then cooled to 0° C. The precipitated crystals were collected by filtration, rinsed on the filter with ethyl acetate and water, and dried to give the title compound as light yellow crystals, m.p. 262°-266° C. Yield 1.29 g.

Workup

  1. custombeing kept below 10° C
  2. temperaturecooled to 0° C
  3. filtrationThe precipitated crystals were collected by filtration
  4. washrinsed on the
  5. filtrationfilter with ethyl acetate and water
  6. customdried

Sources & evidence

ORD record
ord-cf84dc4e2e7e4d9d8b1c74191c77ec52
Source dataset
uspto-grants-1994_12
Patent number
US05371080

Reaction notes

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