N,1-dimethylpyrrolidin-3-amine → HCID 178480456、化合物

HRID 77102

反応式

HRID 77102 の反応式
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]

参加物

4

反応物 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、化合物

生成物 1

HCID 178480456HCID 178480456、化合物収率 30%

反応条件

温度
35 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5a847595c8984844a698703d86c9781a
出典データセット
uspto-grants-2014_09
特許番号
US08835648B2

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