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

HRID 990998Notes

Reaction equation

HRID 990998 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-60df7400a7a24ef7b22ae86094068b08
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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