Water → HCID 16051009, compound

HRID 1591826Notes

Reaction equation

HRID 1591826 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:13]([CH3:14])[C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)=[C:4]([F:17])[CH:3]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>N1C=CC=CC=1.C(OCC)(=O)C>[C:15]([C:12]1[N:13]([CH3:14])[C:9]([C:5]2[C:4]([F:17])=[CH:3][C:2]([NH:1][S:19]([CH3:18])(=[O:21])=[O:20])=[C:7]([F:8])[CH:6]=2)=[CH:10][CH:11]=1)#[N:16]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 160504335-(4-Amino-2,5-difluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16051009HCID 16051009, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-amino-2,5-difluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.15 g, 0.64 mmol) was dissolved in pyridine (2.0 mL). Methanesulfonyl chloride (46 μL, 0.6 mmol) was added and the mixture was stirred for 16 hours, followed by the addition of water. The mixture was diluted with ethyl acetate, washed with water, saturated CuSO4, 2N HCl, brine, dried over MgSO4, and concentrated. The crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-50% ethyl acetate in hexane) to afford 0.142 g of N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2,5-difluorophenyl]-methane-sulfonamide.

Workup

  1. washwashed with water, saturated CuSO4, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7fd9851840e440c99f1d81425b9164b4
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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