N-Methylaniline → US10273222, Example 58

HRID 2277502

反応式

HRID 2277502 の反応式
CS(O[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([C:19]([O:21]C)=[O:20])[CH:16]=[CH:15][N:14]=2)[N:10]=[CH:9]1)(=O)=O.[CH3:23][NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[CH3:23][N:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[CH:15][N:14]=2)[N:10]=[CH:9]1

参加物

4

反応物 2

HCID 7515N-MethylanilineHCID 90407071methyl 2-(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-imidazol-4-yl)pyridine-4-carboxylate

生成物 1

HCID 90407349US10273222, Example 58収率 41%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of methyl 2-(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-imidazol-4-yl)pyridine-4-carboxylate (100 mg, 0.31 mmol) and N-methylaniline (328 mg, 3.1 mmol) in toluene (5 mL) was heated at 110° C. in a sealed tube for 36 hrs. The solution was concentrated to an oily residue which was dissolved in MeOH (5 mL). To this solution was added 10 N NaOH solution (1 g). The mixture was stirred and refluxed for 1 hr and then cooled to RT. The pH was carefully adjusted to 7 whereupon a precipitate formed. The solid was filtered and dried to give the title compound (41 mg) as an off white solid: 1HNMR (400 MHz, CD3OD): δ 2.79 (3H, s), 3.64 (2H, t, J=4.4 Hz), 4.21 (2H, t, J=4.4 Hz), 6.62 (1H, m), 6.68 (2H, m), 7.18 (2H, m), 7.57 (1H, m), 7.66 (1H, s), 7.84 (1H, s), 8.23 (1H, s), 8.63 (1H, m). [M+H] Calc'd for C18H18N4O2, 323. Found, 323.

後処理

  1. concentrationThe solution was concentrated to an oily residue which
  2. dissolutionwas dissolved in MeOH (5 mL)
  3. additionTo this solution was added 10 N NaOH solution (1 g)
  4. temperaturerefluxed for 1 hr
  5. customformed
  6. filtrationThe solid was filtered
  7. customdried

出典と根拠

ORDレコード
ord-c9401894d76f49cf951bdac1967c07c5
出典データセット
uspto-grants-2015_09
特許番号
US09133166B2

関連ノート

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