Ethanesulfonylchloride, 2-chloro- → (4aS,8aR)-4-(3,4-Dimethoxy-phenyl)-2-(1-ethenesulfonyl-piperidin-4-yl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

HRID 585485Notes

Reaction equation

HRID 585485 reaction equation
Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:18]2[C@@H:27]3[C@@H:22]([CH2:23][CH:24]=[CH:25][CH2:26]3)[C:21](=[O:28])[N:20]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[N:19]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:18]2[C@@H:27]3[C@@H:22]([CH2:23][CH:24]=[CH:25][CH2:26]3)[C:21](=[O:28])[N:20]([CH:29]3[CH2:34][CH2:33][N:32]([S:4]([CH:3]=[CH2:2])(=[O:6])=[O:5])[CH2:31][CH2:30]3)[N:19]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 81531DiisopropylethylamineHCID 68878852(4aS,8aR)-4-(3,4-Dimethoxy-phenyl)-2-piperidin-4-yl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Product 1

HCID 69797859(4aS,8aR)-4-(3,4-Dimethoxy-phenyl)-2-(1-ethenesulfonyl-piperidin-4-yl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 20 mmol of 2-chloroethylsulfonylchloride in 20 ml of dichloromethane is added to a solution of 15 mmol of compound 5c and 25 ml of diisopropylethylamine in 50 ml of dichloromethane. The resulting mixture is stirred at RT for 18 h, after which it is washed first with diluted hydrochloric acid and then with a saturated solution of sodium bicarbonate. After drying over magnesium sulfate and evaporating the solvent, the compound is crystallised from diethyl ether. M. p. 89-90° C.

Workup

  1. washafter which it is washed first with diluted hydrochloric acid
  2. dry with materialAfter drying over magnesium sulfate
  3. customevaporating the solvent
  4. customthe compound is crystallised from diethyl ether

Sources & evidence

ORD record
ord-799bc06de1904f08b86ceebb0e10b122
Source dataset
uspto-grants-2005_08
Patent number
US06933296B2

Reaction notes

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