3-[2-(Dimethylamino)ethoxy]aniline → N-[3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}-4-fluoropyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide

HRID 1159971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159971
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH:24][C:25](=[O:34])[C:26]4[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=4[F:33])[CH:21]=[CH:22][CH:23]=3)=[N:10][N:11]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[CH3:35][N:36]([CH3:47])[CH2:37][CH2:38][O:39][C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][CH:46]=1)[NH2:43]>C(O)(C)C.Cl>[CH3:35][N:36]([CH3:47])[CH2:37][CH2:38][O:39][C:40]1[CH:41]=[C:42]([NH:43][C:2]2[N:7]=[C:6]([C:8]3[C:9]([C:18]4[CH:19]=[C:20]([NH:24][C:25](=[O:34])[C:26]5[C:27]([F:33])=[CH:28][CH:29]=[CH:30][C:31]=5[F:32])[CH:21]=[CH:22][CH:23]=4)=[N:10][N:11]4[CH:12]=[CH:13][CH:14]=[C:15]([F:17])[C:16]=34)[CH:5]=[CH:4][N:3]=2)[CH:44]=[CH:45][CH:46]=1

Komponenten

5

Edukt 2

HCID 167782053-[2-(Dimethylamino)ethoxy]anilineHCID 59513881N-{3-[3-(2-chloro-4-pyrimidinyl)-6-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide

Produkt 1

HCID 59513725N-[3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}-4-fluoropyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To the solution of N-{3-[3-(2-chloro-4-pyrimidinyl)-6-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (0.09 g) in isopropanol (5 mL) was added 3-{[2-(dimethylamino)ethyl]oxy}aniline (0.07 g) and 3 drops of concentrated hydrochloric acid. The reaction was microwaved in a sealed tube at 180° C. for 10 min. The isopropanol was removed by rotaevaporation and the residue was treated with sat. NaHCO3 (5 mL), extracted with EtOAc (2×5 mL), and dried (Na2SO4). Concentration and purification with column chromatography afforded the title compound as a yellow solid (0.11 g, 93% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.30 (d, J=2.7 Hz, 6H), 2.70 (t, J=5.7 Hz, 2H), 4.01-4.07 (m, 2H), 6.58-6.68 (m, 2H), 6.95-7.03 (m, 2H), 7.10 (d, J=7.9 Hz, 1H), 7.17-7.30 (m, 4H), 7.37-7.50 (m, 4H), 7.80 (s, 1H), 7.93 (d, J=7.9 Hz, 1H), 8.20 (dd, J=5.2, 2.8 Hz, 1H), 8.39-8.48 (m, 2H); ESIMS (M+H)+=624.

Aufarbeitung

  1. customThe reaction was microwaved in a sealed tube at 180° C. for 10 min
  2. customThe isopropanol was removed by rotaevaporation
  3. additionthe residue was treated with sat. NaHCO3 (5 mL)
  4. extractionextracted with EtOAc (2×5 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration and purification with column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-90d5eb98786c44139e2831cb7390cace
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812022B2

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