Sodium hydride → 3-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-6-methoxy-5-morpholino-imidazo[1,5-a]quinazoline

HRID 1491614Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[N:6][C:7]1[N:8]2[CH:13]=[N:14][C:15]=1[C:16](=[N:18][OH:19])[NH2:17].[CH:26]1([C:29](OCC)=O)[CH2:28][CH2:27]1.[H-].[Na+]>CN(C=O)C.C(O)(=O)C.C(Cl)Cl>[CH:26]1([C:29]2[O:19][N:18]=[C:16]([C:15]3[N:14]=[CH:13][N:8]4[C:9]5[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=5)[C:5]([N:20]5[CH2:21][CH2:22][O:23][CH2:24][CH2:25]5)=[N:6][C:7]=34)[N:17]=2)[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-methoxy-5-morpholino-imidazo[1,5-a]quinazoline-3-carboxamide oxime (0.9 g), ethyl cyclopropylcarboxylate (1.7 g), molecular sieves (3 g), and 80% sodium hydride (0.1 g) in 20 ml of dry DMF was heated for 11/2 hours at 120° C. The mixture was cooled to room temperature, diluted with acetic acid (0.5 ml) and methylene chloride (20 ml) and filtered. The filtered mixture was evaporated and the residue was purified by column chromatography (HPLC) (eluent: methylene chloride:acetone (2:1)) to give yellow crystals of the title compound, m.p. 227°-228° C. Yield 0.38 g.

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered
customThe filtered mixture was evaporated
customthe residue was purified by column chromatography (HPLC) (eluent: methylene chloride:acetone (2:1))

Sources & evidence

ORD record: ord-5362b9ec91984a35a4f9921d240e0756
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05371080

Reaction notes

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