Hydrochloric Acid → 5-(3-{2-[(3-{[2-(Dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}imidazo-[1,2-a]pyridin-2-yl)-2-(methyloxy)benzonitrile

HRID 419311노트

반응식

HRID 419311 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:17]2[CH:18]=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH:24]=2)[C:22]#[N:23])[CH:5]=[CH:4][N:3]=1.Cl.Cl.[CH3:29][N:30]([CH3:41])[CH2:31][CH2:32][O:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37].Cl.C([O-])(O)=O.[Na+]>C(O)C(F)(F)F>[CH3:29][N:30]([CH3:41])[CH2:31][CH2:32][O:33][C:34]1[CH:35]=[C:36]([NH:37][C:2]2[N:7]=[C:6]([C:8]3[N:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]4=[N:10][C:9]=3[C:17]3[CH:18]=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH:24]=3)[C:22]#[N:23])[CH:5]=[CH:4][N:3]=2)[CH:38]=[CH:39][CH:40]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 594527785-[3-(2-Chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-2-(methyloxy)-benzonitrileHCID 66649609[2-(3-Aminophenoxy)ethyl]dimethylamine dihydrochloride

생성물 1

HCID 594528045-(3-{2-[(3-{[2-(Dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}imidazo-[1,2-a]pyridin-2-yl)-2-(methyloxy)benzonitrile수율 93%

시약·촉매·용매 1

HCID 64092,2,2-Trifluoroethanol용매

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온도
84 °C

실험 절차

To 5-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-2-(methyloxy)benzonitrile (Intermediate Example 4) (2.02 g, 5.57 mmol) and 3-{[2-(dimethylamino)ethyl]-oxy}aniline dihydrochloride (1.67 g, 6.58 mmol) in trifluoroethanol (20 mL) was added HCl (0.700 mL, 4M in dioxane, 2.8 mmol). The reaction was stirred at 84° C. for 2 days. The reaction was poured into half saturated NaHCO3, extracted with DCM and EtOAc, dried (MgSO4), concentrated and triturated with diethyl ether to provide the title compound (2.63 g, 5.18 mmol, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.17 (s, 6H), 2.57 (t, J=5.7 Hz, 2H), 3.96 (s, 5H), 6.55 (d, J=8.4 Hz, 1H), 6.63 (d, J=5.1 Hz, 1H), 7.07 (t, J=7.0 Hz, 1H), 7.16 (t, J=8.1 Hz, 1H), 7.26 (d, J=8.4 Hz, 1H), 7.33 (d, J=9.2 Hz, 1H), 7.45-7.53 (m, 2H), 7.74 (d, J=9.2 Hz, 1H), 7.92 (dd, J=9.0, 2.0 Hz, 1H), 7.99 (d, J=1.8 Hz, 1H), 8.39 (d, J=5.1 Hz, 1H), 9.49 (d, J=6.2 Hz, 1H), 9.77 (s, 1H).

후처리

  1. extractionextracted with DCM and EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customtriturated with diethyl ether

출처 및 근거

ORD 기록
ord-7f341b1b3e0245d3ad78157f0c6a7405
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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