4-Methylmorpholine → 2-[3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl]-N-[4-(trifluoromethyl)phenyl]acetamide

HRID 1667255ノート

反応式

HRID 1667255 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](O)=[O:15])[C:9]2=[O:17])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[F:31][C:32]([F:41])([F:40])[C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1.CN1CCOCC1>ClCCl.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14]([NH:37][C:36]3[CH:38]=[CH:39][C:33]([C:32]([F:31])([F:40])[F:41])=[CH:34][CH:35]=3)=[O:15])[C:9]2=[O:17])=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 99644-(Trifluoromethyl)anilineHCID 65578Oxalyl chlorideHCID 673571912-(3,3-Bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid

生成物 1

HCID 674461242-[3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl]-N-[4-(trifluoromethyl)phenyl]acetamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (0.200 g, 0.604 mmol; Example 58D) in dichloromethane (2 mL) was added a catalytic amount of N,N-dimethylformamide followed by oxalyl dichloride (2.0 Min dichloromethane) (0.453 mL, 0.905 mmol). After stirring for 30 minutes, the reaction was concentrated. The residue was dissolved in dichloromethane (2 mL) and 4-(trifluoromethyl)aniline (0.056 mL, 0.453 mmol) followed by 4-methylmorpholine (0.100 mL, 0.905 mmol) were added. After stirring for 1 hour, the reaction was loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 65% ethyl acetate/hexanes (Flow=30 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.37 (s, 1H), 7.51 (d, J=8.6, 2H), 7.40 (d, J=8.5, 2H), 7.34-7.27 (m, 4H), 7.06-6.96 (m, 4H), 4.16 (s, 2H), 3.60 (t, J=6.5, 2H), 2.82 (t, J=6.5, 2H); MS (ESI+) m/z 474.8 (M+H)+.

後処理

  1. concentrationthe reaction was concentrated
  2. dissolutionThe residue was dissolved in dichloromethane (2 mL)
  3. additionwere added
  4. stirringAfter stirring for 1 hour
  5. washthe product eluted with a gradient of 5% ethyl acetate/hexanes to 65% ethyl acetate/hexanes (Flow=30 mL/minute) over 30 minutes

出典と根拠

ORDレコード
ord-70e8070d70ca4ef2a8ae8b1745018c56
出典データセット
uspto-grants-2011_10
特許番号
US08044069B2

反応ノート

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