Methanesulfonyl chloride → HCID 18346038, compound

HRID 1835268Notes

Reaction equation

HRID 1835268 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C@H:13]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=2)=[O:19])[CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C@H:13]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][S:35]([CH3:34])(=[O:37])=[O:36])[CH:22]=2)=[O:19])[CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 18346039HCID 18346039, compound

Product 1

HCID 18346038HCID 18346038, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

Proceeding as described in Example 13 above, but substituting 3-methoxyphenyl-isocyanate with 3-nitrophenylisocynate gave 1-{1-(R)-[4-(3,4-dichlorobenzyl)-piperidin-1-ylmethyl]-2-methylpropyl}-3-(3-nitrophenyl)urea which was then converted to the corresponding 1-{1-(R)-[4-(3,4-dichlorobenzyl)piperidin-1-ylmethyl]-2-methylpropyl}-3-(3-aminophenyl)urea under catalytic hydrogenation conditions using PtO2 catalyst, followed by reaction with methylsulfonyl chloride to give 1-{1-(R)-[4-(3,4-dichlorobenzyl)-piperidin-1-ylmethyl]-2-methylpropyl}-3-(3-methylsulfonylaminophenyl)urea.

Sources & evidence

ORD record
ord-2938f7a73ec34604b7e11407bbaec01a
Source dataset
uspto-grants-2004_08
Patent number
US06770650B2

Reaction notes

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