N,N-Dimethylpiperidin-4-amine → HCID 66977664、化合物

HRID 77106

反応式

HRID 77106 の反応式
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

参加物

5

反応物 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

生成物 2

HCID 222AmmoniaHCID 66977664HCID 66977664、化合物収率 74.8%

反応条件

温度
35 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-59a2a3a174474170904c8e35fd4bc755
出典データセット
uspto-grants-2014_09
特許番号
US08835648B2

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