HCID 18953493, compound → HCID 18953530, compound

HRID 1491608Notes

Reaction equation

HRID 1491608 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[C:18]([F:21])([F:20])[F:19])[N:3]=1.[CH:22]1([C:25]2[N:29]=[C:28]([CH2:30][N+:31]#[C-:32])[O:27][N:26]=2)[CH2:24][CH2:23]1.CC(C)([O-])C.[K+]>CN(C=O)C>[CH:22]1([C:25]2[N:29]=[C:28]([C:30]3[N:31]=[CH:32][N:3]4[C:4]5[C:9](=[C:8]([C:18]([F:21])([F:20])[F:19])[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:27][N:26]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 18953493HCID 18953493, compoundHCID 229129243-Cyclopropyl-5-(isocyanomethyl)-1,2,4-oxadiazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 18953530HCID 18953530, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-chloro-4-morpholino-5-trifluoromethyl-quinazoline (600 mg, 1.9 mmol) and 3-cyclopropyl-5-isocyanomethyl-1,2,4-oxadiazole (440 mg, 2.9 mmol) in dry DMF (15 ml) under nitrogen at 5°-10° C. was added solid potassium t-butoxide (330 mg, 2.9 mmol). The mixture was stirred at 5°-10° C. for 0.5 h and triturated with water (20 ml). The crystals were filtered off and washed with water (10 ml) and ethyl acetate. A final purification was done by stirring the crystals in acetone (10 ml) to give 330 mg of the title compounds, m.p. 197°-199° C.

Workup

  1. customtriturated with water (20 ml)
  2. filtrationThe crystals were filtered off
  3. washwashed with water (10 ml) and ethyl acetate
  4. customA final purification
  5. stirringby stirring the crystals in acetone (10 ml)

Sources & evidence

ORD record
ord-f1dd26400ed24d58b3a4b70e9e607ab2
Source dataset
uspto-grants-1994_12
Patent number
US05371080

Reaction notes

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