4-Methoxybenzenesulfonyl chloride → HCID 69684260, compound

HRID 348543Notes

Reaction equation

HRID 348543 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]3=[O:21])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:9]2[CH2:10][CH2:11][N:12]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]3=[O:21])[CH2:13][CH2:14]2)[S:30]([C:27]2[CH:26]=[CH:25][C:24]([O:23][CH3:22])=[CH:29][CH:28]=2)(=[O:32])=[O:31])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 69684557HCID 69684557, compound

Product 1

HCID 69684260HCID 69684260, compound

Procedure

The title compound, MS (ISP): m/e=539.4 (M+H+), was prepared as for example 99, steps (A) to (F). Step (B) was performed using 4-fluoro-aniline, and yielded (+/−)-trans-2-[4-(4-fluoro-phenylamino)-piperidin-1-yl]-cyclohexanol, which was oxidized to (+/−)-2-[4-(4-fluoro-phenylamino)-piperidin-1-yl]-cyclohexanone in step (C). This was then reacted with 4-methoxy-benzensulfonyl chloride in step (D), yielding (+/−)-N-(4-fluoro-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-cb35cceb94624515b0f3de9e67160fe5
Source dataset
uspto-grants-2007_02
Patent number
US07176316B2

Reaction notes

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