4-Methoxybenzenesulfonyl chloride → HCID 86594084, compound

HRID 348544Notes

Reaction equation

HRID 348544 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]3=[O:22])[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH:10]2[CH2:11][CH2:12][N:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]3=[O:22])[CH2:14][CH2:15]2)[S:33]([C:30]2[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=2)(=[O:35])=[O:34])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 86594085HCID 86594085, compound

Product 1

HCID 86594084HCID 86594084, compound

Procedure

The title compound, MS (ISP): m/e=589.4 (M+H+), was prepared as for example 99, steps (A) to (F). Step (B) was performed using 4-trifluoromethyl-aniline, and yielded (+/−)-trans-2-[4-(4-trifluoromethyl-phenylamino)-piperidin-1-yl]-cyclohexanol, which was oxidized to (+/−)-2-[4-(4-trifluoromethyl-phenylamino)-piperidin-1-yl]-cyclohexanone in step (C). This was then reacted with 4-methoxy-benzensulfonyl chloride in step (D), yielding (+/−)-N-(4-trifluoromethyl-phenyl)-4-methoxy-N-[1-(2-oxo-cyclohexyl)-piperidin-4-yl]-benzenesulfonamide. The final step (F) was performed with bromobenzene.

Sources & evidence

ORD record
ord-5c6f67a06c5246989f7eda4bb13d26c4
Source dataset
uspto-grants-2007_02
Patent number
US07176316B2

Reaction notes

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