Water → N-(5-Phenylethynyl-pyridin-3-yl)-methanesulfonamide

HRID 606920Notes

Reaction equation

HRID 606920 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.Cl.[C:8]1([C:14]#[C:15][C:16]2[CH:17]=[C:18]([NH2:22])[CH:19]=[N:20][CH:21]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CC=CC=1.O>ClCCl>[C:8]1([C:14]#[C:15][C:16]2[CH:17]=[C:18]([NH:22][S:2]([CH3:1])(=[O:4])=[O:3])[CH:19]=[N:20][CH:21]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 670476975-Phenylethynyl-pyridin-3-ylamine dihydrochloride

Product 1

HCID 67047793N-(5-Phenylethynyl-pyridin-3-yl)-methanesulfonamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methanesulfonyl chloride (0.035 mL, 0.45 mmol) to a solution of 5-phenylethynyl-pyridin-3-ylamine dihydrochloride, (prepared as described in EXAMPLE 155), (0.120 g, 0.45 mmol) and pyridine (0.075 mL, 0.90 mmol) in dichloromethane (2.5 mL) at 0° C. Warm to room temperature and stir overnight. Add pyridine (0.020 mL, 0.24 mmol) and methanesulfonyl chloride (0.010 mL, 0.11 mmol), stir for 20 h and add water. Separate the layers and concentrate the organic phase. Purify by silica gel chromatography, eluting with 1.1 hexanes:ethyl acetate, to give the title compound (0.091 g, 75%).

Workup

  1. customSeparate the layers
  2. concentrationconcentrate the organic phase
  3. customPurify by silica gel chromatography
  4. washeluting with 1.1 hexanes

Sources & evidence

ORD record
ord-1618e591cce1401cbc1c3458dc1ec357
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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