Triethylamine → HCID 67508055, compound

HRID 2172874Notes

Reaction equation

HRID 2172874 reaction equation
[Cl:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].[CH2:25](N(CC)CC)C>C(Cl)Cl.O>[Cl:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:21]([CH:20]=[CH2:25])(=[O:23])=[O:22])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67508982HCID 67508982, compound

Product 1

HCID 67508055HCID 67508055, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-6-(piperazin-1-yl)-2,2′-bipyridine (197 mg, 0.717 mmol) in CH2Cl2 (7 mL) was added methanesulfonylchloride (0.0820 mL, 0.789 mmol) followed by triethylamine (0.110 mL, 0.789 mmol) and stirred at RT for 2 h. The reaction mixture was diluted with H2O (30 mL) and extracted with dichloromethane (2×30 mL), dried over sodium sulfate, and concentrated under reduced pressure. The crude mixture was purified by column chromatography (10-50% ethyl acetate/heptane) and obtained the title compound as a white solid (68 mg, 26% yield). LCMS (M+H)+: 365.0.

Workup

  1. extractionextracted with dichloromethane (2×30 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude mixture was purified by column chromatography (10-50% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-8c2169edccdd4cd5ae6bc7f12d034250
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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