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

HRID 1491614ノート

反応式

HRID 1491614 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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))

出典と根拠

ORDレコード
ord-5362b9ec91984a35a4f9921d240e0756
出典データセット
uspto-grants-1994_12
特許番号
US05371080

反応ノート

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