Water → N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-fluorophenyl]ethane sulfonamide

HRID 1591821ノート

反応式

HRID 1591821 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[F:16].[CH2:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18].O>N1C=CC=CC=1.C(OCC)(=O)C>[C:14]([C:11]1[N:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:19]([CH2:17][CH3:18])(=[O:21])=[O:20])=[C:3]([F:16])[CH:4]=2)=[CH:9][CH:10]=1)#[N:15]

参加物

6

反応物 3

HCID 962WaterHCID 11667Ethanesulfonyl chlorideHCID 156045005-(4-amino-3-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

生成物 1

HCID 16051004N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-fluorophenyl]ethane sulfonamide収率 31.8%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-(4-amino-3-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.31 g, 1.44 mmol) was dissolved in pyridine (3 mL), ethane sulfonyl chloride (0.12 mL, 1.3 mmol) was added, the mixture was stirred for 4 hours, and then water was added. The mixture diluted with ethyl acetate and the mixture was washed with water, saturated CuSO4, 2N HCl, brine, dried over MgSO4, and concentrated. Flash chromatography (5%-50% ethyl acetate in hexane) afforded N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-fluorophenyl]ethane sulfonamide (0.127 g). HPLC purity 100% at 210-370 nm, 8.3 min.; the Xterra™ RP18 instrument, 3.5/, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (Ammon. Form. Buff. Ph=3.5/ACN+MeOH) for 10 min., hold 4 min. HRMS: calcd for C14H14FN3O2S+H+, 308.08635; found (ESI, [M+H]+), 308.0855.

後処理

  1. washthe mixture was washed with water, saturated CuSO4, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-0865442f45f44297aedc078fa717964f
出典データセット
uspto-grants-2007_11
特許番号
US07291643B2

反応ノート

読み込み中…