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

HRID 2172861노트

반응식

HRID 2172861 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 22242641Methanol--water (1/1)용매

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온도
25 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a1bef6ae940049f78190d675abecf002
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056865B2

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