4-(5-(4-(2,5-Bis(4-nitrophenyl)pyrrolidin-1-yl)phenyl)pyridin-2-yl)morpholine → 4,4'-(1-(4-(6-Morpholinopyridin-3-yl)phenyl)pyrrolidine-2,5-diyl)dianiline

HRID 1470982ノート

反応式

HRID 1470982 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[N:11]2[C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[CH:32][C:33]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[N:34][CH:35]=3)=[CH:26][CH:25]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C1COCC1.[Pt](=O)=O>[O:39]1[CH2:40][CH2:41][N:36]([C:33]2[N:34]=[CH:35][C:30]([C:27]3[CH:26]=[CH:25][C:24]([N:11]4[CH:12]([C:15]5[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=5)[CH2:13][CH2:14][CH:10]4[C:7]4[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=4)=[CH:29][CH:28]=3)=[CH:31][CH:32]=2)[CH2:37][CH2:38]1

参加物

5

反応物 2

HCID 867623254-(5-(4-(2,5-Bis(4-nitrophenyl)pyrrolidin-1-yl)phenyl)pyridin-2-yl)morpholineHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 672367054,4'-(1-(4-(6-Morpholinopyridin-3-yl)phenyl)pyrrolidine-2,5-diyl)dianiline収率 65%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒3 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

Charged a 100-mL round bottom flask with the product of Example 108A (174.7 mg, 0.317 mmol), partially dissolved in THF (12.50 mL) and absolute EtOH (2.50 mL), evacuated on house vacuum and filled flask with nitrogen, then added platinum (IV) oxide (14.38 mg, 0.063 mmol), evacuated flask on house vacuum and filled with hydrogen from a balloon, repeated evacuation/filling cycle 3 times, and stirred heterogeneous reaction mixture vigorously under hydrogen (1 atm). After 2 hr, charged reaction with additional platinum (IV) oxide (14.38 mg, 0.063 mmol) and continued to vigorously stir under hydrogen at 25° C. After 5 hr, added additional platinum (IV) oxide (14.38 mg, 0.063 mmol). The reaction mixture was then vacuum filtered through a bed of Celite 545 in a Büchner funnel, the filter pad was washed with CHCl3 (100 mL) and hot CHCl3 (2×50 mL), and the filtrate concentrated by rotary evaporation to give the title compound as a yellow solid (101 mg, 65%) as a mixture of stereoisomers. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.71-1.87 (m, 2H), 2.24-2.31 (m, 1H), 3.37-3.45 (m, 4H), 3.64-3.74 (m, 4H), 4.57 (t, J=4.99 Hz, 2H), 4.95 (s, 4H), 6.42-6.53 (m, 3H), 6.57 (d, J=8.35 Hz, 4H), 6.76-6.89 (m, 2H), 7.15 (d, J=8.35 Hz, 4H), 7.26 (d, J=8.78 Hz, 2H), 7.68 (dd, J=8.84, 2.44 Hz, 1H), 8.29 (d, J=2.39 Hz, 1H); MS (ESI+) m/z 492 (M+H)+.

後処理

  1. customabsolute EtOH (2.50 mL), evacuated on house vacuum
  2. additionfilled flask with nitrogen
  3. additioncharged
  4. waitAfter 5 hr
  5. filtrationvacuum filtered through a bed of Celite 545 in a Büchner funnel
  6. washthe filter pad was washed with CHCl3 (100 mL) and hot CHCl3 (2×50 mL)
  7. concentrationthe filtrate concentrated by rotary evaporation

出典と根拠

ORDレコード
ord-d048f752623a48aabf6dabc4660f1136
出典データセット
uspto-grants-2015_04
特許番号
US09006387B2

反応ノート

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