Triethylamine → (r)-2,5-Dimethyl-furan-3-sulfonic acid [1-(5'-fluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-amide

HRID 2422849ノート

反応式

HRID 2422849 の反応式
C(N(CC)CC)C.[CH3:8][C:9]1[O:10][C:11]([CH3:18])=[CH:12][C:13]=1[S:14](Cl)(=[O:16])=[O:15].[F:19][C:20]1[CH:21]=[CH:22][C:23]([O:35][CH3:36])=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]([NH2:34])[CH3:33])=[CH:28][CH:27]=2)[CH:25]=1>ClCCl>[F:19][C:20]1[CH:21]=[CH:22][C:23]([O:35][CH3:36])=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C@H:32]([NH:34][S:14]([C:13]3[CH:12]=[C:11]([CH3:18])[O:10][C:9]=3[CH3:8])(=[O:16])=[O:15])[CH3:33])=[CH:28][CH:27]=2)[CH:25]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27950242,5-dimethylfuran-3-sulfonyl ChlorideHCID 610332941-(5'-Fluoro-2'-methoxy-biphenyl-4-yl)-ethylamine

生成物 1

HCID 24768970(r)-2,5-Dimethyl-furan-3-sulfonic acid [1-(5'-fluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-amide収率 11.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (41.1 μl, 0.295 mmol) then 2,5-dimethyl-3-furansulfonyl chloride (19.1 mg, 0.0982 mmol) were added to a solution of 1-(5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (20 mg, 0.082 mmol) in dichloromethane (1 ml) and the resulting solution shaken at room temperature overnight. The reaction mixture was washed with saturated sodium bicarbonate solution (500 μl) and the organic phase separated, dried over anhydrous magnesium sulfate and the solvent evaporated. The crude product was purified by preparatory LCMS. The solvent was evaporated under reduced pressure to give the title compound (3.9 mg, 0.0097 mmol, 11.8%). 1H NMR (400 MHz, CDCl3): δ 7.40, 7.23 (a/b, 4H), 7.05-6.88 (m, 3H), 5.99 (s, 1H), 4.67 (m, 1H), 4.55 (m, 1H), 3.78 (s, 3H), 2.35 (s, 3H), 2.17 (s, 3H), 1.52 (d, 3H) ppm; MS (ESI) m/z: 426 [M+Na]+.

後処理

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution (500 μl)
  2. customthe organic phase separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent evaporated
  5. customThe crude product was purified by preparatory LCMS
  6. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-ac92e589f10a4fd6a71836dce0228a65
出典データセット
uspto-grants-2011_06
特許番号
US07960365B2

反応ノート

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