Water → 6-(3-Chloro-2,6-dimethoxyphenyl)-1-(3-(2-methylthiazol-4-yl)benzyl)piperidin-2-one

HRID 594664Notes

Reaction equation

HRID 594664 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[N:25]=[C:26]([CH3:29])[S:27][CH:28]=3)[CH:19]=2)[C:15](=[O:30])[CH2:14][CH2:13][CH2:12]1.C1C(=O)N([Cl:38])C(=O)C1.O.CCOC(C)=O>CN(C=O)C>[Cl:38][C:8]1[C:3]([O:2][CH3:1])=[C:4]([CH:11]2[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[N:25]=[C:26]([CH3:29])[S:27][CH:28]=4)[CH:19]=3)[C:15](=[O:30])[CH2:14][CH2:13][CH2:12]2)[C:5]([O:9][CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 690825166-(2,6-Dimethoxyphenyl)-1-(3-(2-methylthiazol-4-yl)benzyl)piperidin-2-one

Product 1

HCID 690826986-(3-Chloro-2,6-dimethoxyphenyl)-1-(3-(2-methylthiazol-4-yl)benzyl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(2,6-dimethoxyphenyl)-1-(3-(2-methylthiazol-4-yl)benzyl)piperidin-2-one (60 mg; 0.14 mmol; compound corresponding to example 16), and NCS (21 mg; 0.15 mmol) in anh. DMF (1.5 ml) was stirred at rt, under nitrogen, for 24 h. Water (5 ml), and AcOEt (10 ml) were added, and the separated organic layer was washed with brine (5 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure.

Workup

  1. washthe separated organic layer was washed with brine (5 ml)
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7b85db242eb948ff849adcee61e6aa43
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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