Hydrochloric Acid → N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3,5-difluorophenyl]-methanesulfonamide

HRID 1591850Notes

Reaction equation

HRID 1591850 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([C:14]2[N:18]([CH3:19])[C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[C:9]([F:22])[CH:8]=1.Cl>N1C=CC=CC=1>[C:20]([C:17]1[N:18]([CH3:19])[C:14]([C:10]2[C:9]([F:22])=[CH:8][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:12][C:11]=2[F:13])=[CH:15][CH:16]=1)#[N:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 160505305-(4-amino-2,6-difluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16051282N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3,5-difluorophenyl]-methanesulfonamideYield 45%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methanesulfonyl chloride (0.046 mL, 0.66 mmol) and 5-(4-amino-2,6-difluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.100 g, 0.429 mmol) in pyridine (1.5 mL) was heated to 50° C. for 4 hours. The reaction mixture was acidified with 1N HCl solution and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (dichloromethane/acetone, 97/3) to afford the title compound (0.060 g, 45%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (dichloromethane/acetone, 97/3)

Sources & evidence

ORD record
ord-ebf830a1b77f4c31bda5e9273b862c88
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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