1,2,4-Oxadiazole, 5-cyclopropyl-3-(isocyanomethyl)- → HCID 19784292, compound

HRID 256820Notes

Reaction equation

HRID 256820 reaction equation
Cl[C:2]1[N:11]2[CH:12]=[N:13][N:14]=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[CH:15]1([C:18]2[O:22][N:21]=[C:20]([CH2:23][N+:24]#[C-:25])[N:19]=2)[CH2:17][CH2:16]1.CC(C)([O-])C.[K+]>CN(C=O)C>[CH:15]1([C:18]2[O:22][N:21]=[C:20]([C:23]3[N:24]=[CH:25][N:3]4[C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=5[C:10]5=[N:14][N:13]=[CH:12][N:11]5[C:2]=34)[N:19]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 107493421,2,4-Oxadiazole, 5-cyclopropyl-3-(isocyanomethyl)-HCID 19784289HCID 19784289, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19784292HCID 19784292, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred slurry of 5-chloro-1,2,4-triazolo[4,3-c]quinazoline (3.5 g, 17 mmol) in 40 ml of dry DMF at 10° C. was first added 5-cyclopropyl-3-isocyanomethyl-1,2,4-oxadiazole (purity 80%, 3.4 g, 18 mmol) and then a solution of potassium tert-butoxide (2.55 g, 23 mmol) in 40 ml of DMF, allowing the temperature to rise to room temperature. After 1/2 h the mixture was filtered and the filter cake washed with water and finally with ether and dried, giving the title compound as colorless crystals, m.p. 308°-314° C.

Workup

  1. customat 10° C.
  2. customto rise to room temperature
  3. filtrationAfter 1/2 h the mixture was filtered
  4. washthe filter cake washed with water and finally with ether
  5. customdried

Sources & evidence

ORD record
ord-3f375894f7a748f39b14daceb4748d3c
Source dataset
uspto-grants-1993_11
Patent number
US05260298

Reaction notes

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