Oxalyl chloride → 2-Morpholinoethyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-benzoate

HRID 990998ノート

反応式

HRID 990998 の反応式
[N:1]1([C:13]2C=CC(C(Cl)=O)=C[CH:14]=2)[C:5]2C3C(C[C:4]=2C=N1)=CC=CC=3.[NH:22]1[C:26]2[C:27]3[C:32]([CH2:33][C:25]=2[C:24]([C:34]2[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=2)=[N:23]1)=[CH:31][CH:30]=[CH:29][CH:28]=3.[C:43](Cl)(=[O:47])[C:44](Cl)=O>ClCCl.CN(C=O)C>[NH:22]1[C:26]2[C:27]3[C:32]([CH2:33][C:25]=2[C:24]([C:34]2[CH:42]=[CH:41][C:37]([C:38]([O:40][CH2:4][CH2:5][N:1]4[CH2:44][CH2:43][O:47][CH2:14][CH2:13]4)=[O:39])=[CH:36][CH:35]=2)=[N:23]1)=[CH:31][CH:30]=[CH:29][CH:28]=3

参加物

6

反応物 3

HCID 65578Oxalyl chlorideHCID 184158474-(1,4-Dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acidHCID 538774994-(1,4-Dihydroindeno[1,2-c]pyrazol-yl)benzoyl chloride

生成物 1

HCID 184159982-Morpholinoethyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-benzoate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-(1,4-dihydroindeno[1,2-c]pyrazol-yl)benzoyl chloride [(500 mg) prepared by reaction of the product of Example 8 (1.45 g) with oxalyl chloride (1.5 ml) in dichloromethane (100 ml) and DMF (8 drops) followed by evaporation of the solvent], dichloromethane (50 ml), 2-morpholinoethanol (0.22 ml) and triethylamine (0.5 ml) was stirred at ambient temperature for 3.5 hours. The mixture was washed with water then with saturated sodium bicarbonate solution, then dried, filtered and evaporated to give an oil which was purified by flash column chromatography on silica using dichloromethane/IMS (10:1) as the mobile phase to give an oil which was purified again by flash column chromatography using dichloromethane/IMS (25:1) as the mobile phase to give the product 2-morpholinoethyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)- benzoate as a solid, m.p. 168-172° C.

後処理

  1. customfollowed by evaporation of the solvent], dichloromethane (50 ml), 2-morpholinoethanol (0.22 ml) and triethylamine (0.5 ml)
  2. washThe mixture was washed with water
  3. dry with materialwith saturated sodium bicarbonate solution, then dried
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil which
  7. customwas purified by flash column chromatography on silica
  8. customto give an oil which
  9. customwas purified again by flash column chromatography

出典と根拠

ORDレコード
ord-60df7400a7a24ef7b22ae86094068b08
出典データセット
uspto-grants-2002_10
特許番号
US06462036B1

反応ノート

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