Benzoic acid, 3-(chlorosulfonyl)- → HCID 46203370, compound

HRID 524158Notes

Reaction equation

HRID 524158 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[C:13]([CH3:25])([CH3:24])[C:14](=[O:23])[N:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].Cl[S:27]([C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([OH:35])=[O:34])(=[O:29])=[O:28]>>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[C:13]([CH3:25])([CH3:24])[C:14](=[O:23])[N:15]([CH:17]3[CH2:22][CH2:21][N:20]([S:27]([C:30]4[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=4)[C:33]([OH:35])=[O:34])(=[O:29])=[O:28])[CH2:19][CH2:18]3)[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

3

Reactant 2

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 666164065-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 46203370HCID 46203370, compound

Procedure

The title compound is prepared analogously as described for GP1 using 5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one (compound B1) and 3-(chlorosulfonyl)benzoic acid as starting compounds. Instead of using the work-up procedure described for GP1, the following procedure is used. After the reaction has been quenched with 1 M aqueous sodium carbonate solution, the phases are separated and the aqueous phase is slightly acidified with aqueous hydrochloric acid. The aqueous phase is extracted with DCM, the organic phase dried with MgSO4 and the solvent is removed under reduced pressure to yield the title compound.

Workup

  1. customThe title compound is prepared analogously
  2. customAfter the reaction has been quenched with 1 M aqueous sodium carbonate solution
  3. customthe phases are separated
  4. extractionThe aqueous phase is extracted with DCM
  5. dry with materialthe organic phase dried with MgSO4
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-973ccc390b714a559cb5d29784c23fd7
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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