N,1-dimethylpyrrolidin-3-amine → HCID 178480456, 화합물

HRID 77102

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HRID 77102 반응식
Cl.[Cl:2][C:3]1[CH:27]=[CH:26][C:6]2[NH:7][C:8]([C:10]3[CH:11]=[C:12]([N:17]4[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=O)[CH2:19][CH2:18]4)[CH:13]=[CH:14][C:15]=3[F:16])=[N:9][C:5]=2[CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:52][NH:53][CH:54]1[CH2:58][N:57]([CH3:59])[CH2:56][CH2:55]1>>[CH3:52][N:53]([CH:54]1[CH2:55][CH2:56][N:57]([CH3:59])[CH2:58]1)[C:23]([CH:20]1[CH2:21][CH2:22][N:17]([C:12]2[CH:13]=[CH:14][C:15]([F:16])=[C:10]([C:8]3[NH:7][C:6]4[CH:26]=[CH:27][C:3]([Cl:2])=[CH:4][C:5]=4[N:9]=3)[CH:11]=2)[CH2:18][CH2:19]1)=[O:25]

참가 물질

4

반응물 3

HCID 2758520N,1-dimethylpyrrolidin-3-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178479749HCID 178479749, 화합물

생성물 1

HCID 178480456HCID 178480456, 화합물수율 30%

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온도
35 °C

실험 절차

Method J—Step a To a mixture of 1-[3-(5-Chloro-1H-benzoimidazol-2-yl)-4-fluoro-phenyl]-piperidine-4-carboxylic acid hydrochloride (obtained as described in general method 10, step b) (0.01 g, 0.25 mmol) in dcm (2 mL), HATU (0.10 g, 0.26 mmol), TEA (0.07 mL, 0.55 mmol) and N,N′-dimethyl-3-aminopyrrolidine (0.04 g, 0.31 mmol) were added. The reaction mixture was heated at 35° C. overnight, cooled to room temperature and washed with ammonium chloride solution (2 mL), saturated Na2CO3 solution (2 mL) and water (2 mL). The organic layer was then filtrated on an NH2 cartridge and further purified by flash chromatography (eluent: EtOAc:NH3 2N in MeOH/9:1) to obtain 0.03 g of the title compound (30%).

후처리

  1. additionwere added
  2. temperaturecooled to room temperature
  3. washwashed with ammonium chloride solution (2 mL), saturated Na2CO3 solution (2 mL) and water (2 mL)
  4. filtrationThe organic layer was then filtrated on an NH2 cartridge
  5. customfurther purified by flash chromatography (eluent: EtOAc:NH3 2N in MeOH/9:1)

출처 및 근거

ORD 기록
ord-5a847595c8984844a698703d86c9781a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835648B2

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