Potassium Carbonate → 2-methylsulfonylamino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane

HRID 1598555Notes

Reaction equation

HRID 1598555 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3[CH2:18][CH2:19][C:20](=[O:23])[NH:21][N:22]=3)[CH:14]=2)[CH2:9]1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>O.C(OCC)(=O)C.O1CCCC1>[CH3:24][S:25]([NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3[CH2:18][CH2:19][C:20](=[O:23])[NH:21][N:22]=3)[CH:14]=2)[CH2:9]1)(=[O:27])=[O:26]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 140714996-(2-amino-indan-5-yl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 98830312-methylsulfonylamino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indaneYield 70.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.4 g of potassium carbonate dissolved in 20 ml of water was added to 1.15 g of 2-amino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane dissolved in 40 ml of ethyl acetate and 20 ml of tetrahydrofuran. Then, 0.57 g of methanesulfonyl chloride was added thereto and the mixture was stirred for 2 hours. After the organic layer was collected by separation and dried, the solvent was removed. The resulting crystals were recrystallized from tetrahydrofuran-isopropyl ether to obtain 1.08 g of 2-methylsulfonylamino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane.

Workup

  1. customAfter the organic layer was collected by separation
  2. customdried
  3. customthe solvent was removed
  4. customThe resulting crystals were recrystallized from tetrahydrofuran-isopropyl ether

Sources & evidence

ORD record
ord-c2e3d84e720f42a5a9a2c75df8609bfd
Source dataset
uspto-grants-1998_04
Patent number
US05739132

Reaction notes

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