Phenylmethanesulfonyl chloride → N-(1-(4-(4-Chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)(phenyl)methanesulfonamide

HRID 1016100Notes

Reaction equation

HRID 1016100 reaction equation
[CH2:1]([S:8](Cl)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl.[NH2:22][CH:23]([CH:39]([CH3:41])[CH3:40])[C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)=[O:25]>C(Cl)Cl.CO>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH:29]2[CH2:28][CH2:27][N:26]([C:24](=[O:25])[CH:23]([NH:22][S:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)(=[O:10])=[O:9])[CH:39]([CH3:41])[CH3:40])[CH2:31][CH2:30]2)=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 672994912-Amino-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methylbutan-1-one hydrochloride

Product 1

HCID 57888688N-(1-(4-(4-Chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)(phenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A reaction tube was charged with benzylsulfonyl chloride (14 mg), DIEA (50 μL) and 2-amino-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methylbutan-1-one hydrochloride (20 mg) in DCM (0.3 mL). The reaction mixture was shaken overnight at rt. At the conclusion of this period, the resulting solution was diluted with MeOH and purified by preparative LC-MS to provide Example 200. MS found: (M+H)+=450.

Workup

  1. custompurified by preparative LC-MS
  2. customto provide Example 200

Sources & evidence

ORD record
ord-668ed7128d964cf8afce921b0b9e00fb
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

Loading…