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

HRID 990998노트

반응식

HRID 990998 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60df7400a7a24ef7b22ae86094068b08
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06462036B1

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