Pyridine → HCID 59299355, compound

HRID 2235303Notes

Reaction equation

HRID 2235303 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[NH2:19][C:20]1[CH:38]=[C:37]([Cl:39])[C:23]([CH2:24][CH:25]2[CH2:29][CH2:28][N:27]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:26]2=[O:36])=[C:22]([Cl:40])[CH:21]=1>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8]([NH:19][C:20]2[CH:38]=[C:37]([Cl:39])[C:23]([CH2:24][CH:25]3[CH2:29][CH2:28][N:27]([CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[C:26]3=[O:36])=[C:22]([Cl:40])[CH:21]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 59299494HCID 59299494, compound

Product 1

HCID 59299355HCID 59299355, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Place 3-Chloro-2-methyl-benzenesulfonyl chloride (160 mg, 0.70 mmol) in CH2Cl2 (10 mL) and cool to 0° C. Slowly add pyridine (0.06 mL, 0.70 mmol) and stir for 15 minutes. Add 3-(4-Amino-2,6-dichloro-benzyl)-1-cyclohexyl-pyrrolidin-2-one (Example 183), 200 mg, 0.59 mmol) and stir for 12 hours. Quench with 1N HCl and extract with dichloromethane. Wash the extract with NaHCO3, brine. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (10-80% ethyl acetate in hexanes) to afford 181 mg (58%) of the title compound: Mass spectrum (apci) m/z=529.05 (M+H).

Workup

  1. customQuench with 1N HCl
  2. extractionextract with dichloromethane
  3. washWash the
  4. extractionextract with NaHCO3, brine
  5. dry with materialDry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify by silica gel (10-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7ab3a707766746a28dd5bf8d6cfd679c
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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