8-Quinolinesulfonyl chloride → 5-(7-Methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2-[1-(quinolin-8-ylsulfonyl)piperidin-4-yl]-2,4-dihydro-3H-pyrazol-3-one

HRID 1914091Notes

Reaction equation

HRID 1914091 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:12]2[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]=2[C:7]([C:15]2[C:16]([CH3:28])([CH3:27])[C:17](=[O:26])[N:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:19]=2)=[CH:6][CH:5]=1.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][C:37]=2[S:39](Cl)(=[O:41])=[O:40])[CH:32]=[CH:31][CH:30]=1>>[CH3:2][O:3][C:4]1[C:12]2[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]=2[C:7]([C:15]2[C:16]([CH3:28])([CH3:27])[C:17](=[O:26])[N:18]([CH:20]3[CH2:25][CH2:24][N:23]([S:39]([C:37]4[CH:36]=[CH:35][CH:34]=[C:33]5[C:38]=4[N:29]=[CH:30][CH:31]=[CH:32]5)(=[O:40])=[O:41])[CH2:22][CH2:21]3)[N:19]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 292208-Quinolinesulfonyl chlorideHCID 666165905-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 462036765-(7-Methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2-[1-(quinolin-8-ylsulfonyl)piperidin-4-yl]-2,4-dihydro-3H-pyrazol-3-one

Procedure

The title compound is prepared analogously as described for GP1 using 5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one hydrochloride (compound B5*HCl) and quinoline-8-sulfonyl chloride as starting compounds. The crude product is purified by crystallization from methanol to yield the title compound.

Workup

  1. customThe title compound is prepared analogously
  2. customThe crude product is purified by crystallization from methanol

Sources & evidence

ORD record
ord-2c7c78ea46a04f3c9206074b3202d864
Source dataset
uspto-grants-2013_12
Patent number
US08609848B2

Reaction notes

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