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

HRID 1491614노트

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HRID 1491614 반응식
[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

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 78351Ethyl cyclopropanecarboxylateHCID 867482966-Methoxy-5-morpholino-imidazo[1,5-a]quinazoline-3-carboxamide oxime

생성물 1

HCID 189535263-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-6-methoxy-5-morpholino-imidazo[1,5-a]quinazoline

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
120 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5362b9ec91984a35a4f9921d240e0756
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05371080

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