Ammonium Hydroxide → 1-(4-(3,5-Dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one

HRID 2172861ノート

反応式

HRID 2172861 の反応式
Cl[C:2]1[C:3]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][N:23]=2)=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:21])[CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[NH4+].[OH-]>[Pd].CO.O>[CH3:28][C:27]1[C:22]([C:3]2[CH:2]=[CH:7][N:6]=[C:5]([N:8]3[CH2:9][CH2:10][N:11]([C:14](=[O:21])[CH2:15][CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH2:12][CH2:13]3)[CH:4]=2)=[N:23][CH:24]=[C:25]([CH3:29])[CH:26]=1

参加物

5

反応物 2

HCID 14923Ammonium HydroxideHCID 569562401-(4-(5'-Chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one

生成物 1

HCID 569675951-(4-(3,5-Dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one収率 90%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
25 °C

実験手順

To 1-[4-(5′-chloro-3,5-dimethyl-2,4′-bipyridin-2′-yl)piperazin-1-yl]-3-(methylsulfonyl)propan-1-one (44 mg, 0.10 mmol) was added MeOH/Water 6:1 (5 mL, 0.02M), then 10% Pd/C (25 μL=20 w/w % relative to substrate) followed by NH4OH (1.0 mL, 5 eq, 0.5M solution in MeOH). The reaction of mixture was stirred at ambient temperature at 25° C. under balloon H2 for 12 hrs. After filtering off catalyst through celite, the concentrated crude product was diluted with EtOAc (25 mL), washed with water (10 mL), then brine (10 mL), dried over MgSO4, filtered. The solution was concentrated in vacuo. The residue was purified by chromatography on silica gel (EtOAc/heptane=1:3) to give the title compound (36 mg, 90%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.36 (s, 1 H) 8.24-8.29 (m, 1 H) 7.42 (s, 1 H) 6.79-6.84 (m, 2 H) 3.75-3.81 (m, 4 H) 3.58-3.66 (m, 4 H) 3.47 (t, J=7.33 Hz, 2 H) 3.00 (s, 3H) 2.93-2.99 (m, 2 H) 2.37 (s, 3 H) 2.33 (s, 3 H); m/z for C20H26N4O3S 403.1 (M+H)+.

後処理

  1. customThe reaction of mixture
  2. filtrationAfter filtering off catalyst through celite
  3. concentrationthe concentrated crude product
  4. additionwas diluted with EtOAc (25 mL)
  5. washwashed with water (10 mL)
  6. dry with materialbrine (10 mL), dried over MgSO4
  7. filtrationfiltered
  8. concentrationThe solution was concentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (EtOAc/heptane=1:3)

出典と根拠

ORDレコード
ord-a1bef6ae940049f78190d675abecf002
出典データセット
uspto-grants-2015_06
特許番号
US09056865B2

反応ノート

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