1-Methylpyrrolidine → N-(2,6-Diethyl-4-morpholin-4-yl-phenyl)-4-methyl-benzenesulfonamide

HRID 1867298ノート

反応式

HRID 1867298 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([CH2:21][CH3:22])[CH:3]=1.Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br.C(N(CC)C(C)C)(C)C.CN1CCCC1>C(OCC)(=O)C>[CH2:8]([C:6]1[CH:7]=[C:2]([N:1]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:3]=[C:4]([CH2:21][CH3:22])[C:5]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH3:9]

参加物

6

反応物 4

HCID 84541-MethylpyrrolidineHCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 183982Benzenesulfonamide, N-(4-amino-2,6-diethylphenyl)-4-methyl-

生成物 1

HCID 67406337N-(2,6-Diethyl-4-morpholin-4-yl-phenyl)-4-methyl-benzenesulfonamide収率 91%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
180 °C

実験手順

A mixture of N-(4-amino-2,6-diethyl-phenyl)-4-methyl-benzenesulfonamide (70 mg), bis-(2-bromoethyl)ether (33 μL), N,N-diisopropyl-ethylamine (115 μL) and N-methylpyrrolidine (0.3 mL) was heated to 180° C. for 20 minutes in a sealed microwave process vial. The mixture was diluted with ethyl acetate (20 mL), washed with brine (30 mL) and saturated aqueous potassium carbonate (30 mL), and dried over sodium sulfate. The organic phase was concentrated in vacuo to furnish 78 mg (91%) of the title compound. LC-MS (m/z) 389 (MH+); tR=2.77, (UV, ELSD) 57%, 98%. The crude product was used without further purification.

後処理

  1. washwashed with brine (30 mL) and saturated aqueous potassium carbonate (30 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationThe organic phase was concentrated in vacuo

出典と根拠

ORDレコード
ord-b463ee5899984e65b5354a35eb6b3936
出典データセット
uspto-grants-2009_12
特許番号
US07632835B2

反応ノート

読み込み中…