N,N-Dimethylpiperidin-4-amine → HCID 66977664, 화합물

HRID 77106

반응식

HRID 77106 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][N:52]([CH:54]1[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]1)[CH3:53]>>[NH3:3].[CH3:51][N:52]([CH3:53])[CH:54]1[CH2:59][CH2:58][N:57]([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])[CH2:56][CH2:55]1

참가 물질

5

반응물 3

HCID 417391N,N-Dimethylpiperidin-4-amineHCID 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 66977664HCID 66977664, 화합물수율 74.8%

반응 조건

온도
35 °C

실험 절차

Method N—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-(N,N-dimethylamino)piperidine (0.04 g, 0.35 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:NH3 in MeOH (2N)/10:0 to 9:1) to obtain 0.05 g of the title compound (37%).

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-59a2a3a174474170904c8e35fd4bc755
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835648B2

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