Chlorosulfonic acid → 4-Ethoxy-3-(8-cyclopentyl-6-methyl-4-oxo-3,4-dihydro-imidazol[1,5-a][1,3,5]-triazin-2-yl)-benzenesulfonyl chloride

HRID 8622

Reaction equation

HRID 8622 reaction equation
[CH:1]1([C:6]2[N:7]=[C:8]([CH3:25])[N:9]3[C:14](=[O:15])[NH:13][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22][CH2:23][CH3:24])=[N:11][C:10]=23)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:26][S:27](O)(=[O:29])=[O:28]>ClCCl>[CH2:23]([O:22][C:17]1[CH:18]=[CH:19][C:20]([S:27]([Cl:26])(=[O:29])=[O:28])=[CH:21][C:16]=1[C:12]1[NH:13][C:14](=[O:15])[N:9]2[C:8]([CH3:25])=[N:7][C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[C:10]2[N:11]=1)[CH3:24]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1357235138-Cyclopentyl-2-(2-ethoxy-phenyl)-6-methyl-3H-imidazo[1,5-a][1,3,5]triazin-4-one

Product 1

HCID 1357235154-Ethoxy-3-(8-cyclopentyl-6-methyl-4-oxo-3,4-dihydro-imidazol[1,5-a][1,3,5]-triazin-2-yl)-benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

372.3 mg (1.1 mmol) of 8-cyclopentyl-2-(2-ethoxy-phenyl)-6-methyl-3H-imidazo[1,5-a][1,3,5]triazin-4-one (example IX) are added in portions to 0.66 ml (9.9 mmol) of ice-cooled chlorosulfonic acid. The mixture is subsequently stirred overnight at room temperature before being diluted with dichloromethane and poured onto ice water. The organic phase is separated off. The aqueous phase is extracted once again with dichloromethane and the organic phases are combined, dried and evaporated.

Workup

  1. additionpoured onto ice water
  2. customThe organic phase is separated off
  3. extractionThe aqueous phase is extracted once again with dichloromethane
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-6f110095d41b437f9aec3433c29d3d1d
Source dataset
uspto-grants-2006_08
Patent number
US07091203B2

Linked notes

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