4-Methoxypiperidine → (4-Methoxy-piperidin-1-yl)-{(R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidin-3-yl}-methanone

HRID 77105

반응식

HRID 77105 반응식
Cl.[CH3:2][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[CH:13]=[C:14]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24](O)=[O:25])[CH2:19]2)[CH:15]=[CH:16][CH:17]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:51][O:52][CH:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>>[NH3:3].[CH3:51][O:52][CH:53]1[CH2:58][CH2:57][N:56]([C:24]([C@@H:20]2[CH2:21][CH2:22][CH2:23][N:18]([C:14]3[CH:15]=[CH:16][CH:17]=[C:12]([C:4]4[N:3]([CH3:2])[C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=5[N:5]=4)[CH:13]=3)[CH2:19]2)=[O:25])[CH2:55][CH2:54]1

참가 물질

5

반응물 3

HCID 776664-MethoxypiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66977536(R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride

생성물 2

HCID 222AmmoniaHCID 66977804(4-Methoxy-piperidin-1-yl)-{(R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidin-3-yl}-methanone수율 77.1%

반응 조건

온도
35 °C

실험 절차

Method M—Step a To a mixture of (R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride (obtained as described in general method 1, step d) (0.01 g, 0.30 mmol) (obtained as described in method A, step d) in dcm (2.5 mL), HATU (0.12 g, 0.33 mmol), TEA (0.09 mL, 0.63 mmol) and 4-methoxypiperidine (0.04 g, 0.33 mmol) were added. The reaction mixture was heated at 35° C. overnight, cooled to room temperature, washed with ammonium chloride solution (3 mL), filtered through a phase separator and organic solvent was removed. The crude was then purified by SCX column (eluent: first dcm:MeOH/1:1 then NH3 in MeOH (2N)) and flash chromatography (eluent: gradient from EtOAc:cyclohexane/10:0 to 0:10) to obtain 0.05 g of the title compound (38%).

후처리

  1. additionwere added
  2. temperaturecooled to room temperature
  3. washwashed with ammonium chloride solution (3 mL)
  4. filtrationfiltered through a phase separator and organic solvent
  5. customwas removed
  6. customThe crude was then purified by SCX column (eluent

출처 및 근거

ORD 기록
ord-d56fe85f2ba64ac698b8eb550fb3a895
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835648B2

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