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Hydrochloric Acid → N-(2,6-difluorophenyl)-3-{3-[2-({2-(ethyloxy)-4-[4-(1-methylethyl)-1-piperazinyl]phenyl}amino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-2-yl}benzamide

HRID 419543
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 419543
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]=[C:19]([CH:31]=[CH:32][CH:33]=2)[C:20]([NH:22][C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=2[F:30])=[O:21])[CH:5]=[CH:4][N:3]=1.[CH2:34]([O:36][C:37]1[CH:42]=[C:41]([N:43]2[CH2:48][CH2:47][N:46]([CH:49]([CH3:51])[CH3:50])[CH2:45][CH2:44]2)[CH:40]=[CH:39][C:38]=1[NH2:52])[CH3:35].Cl.O1CCOCC1.C[O-].[Na+]>FC(F)(F)CO.CO.C(Cl)Cl.CCCCCC>[F:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([F:29])[C:23]=1[NH:22][C:20](=[O:21])[C:19]1[CH:31]=[CH:32][CH:33]=[C:17]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]3[C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:52][C:38]3[CH:39]=[CH:40][C:41]([N:43]4[CH2:48][CH2:47][N:46]([CH:49]([CH3:50])[CH3:51])[CH2:45][CH2:44]4)=[CH:42][C:37]=3[O:36][CH2:34][CH3:35])[N:7]=2)[CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 10942334Sodium MethoxideHCID 59452785(2-(Ethyloxy)-4-[4-(1-methylethyl)-1-piperazinyl]phenyl}amineHCID 594529693-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-benzamide

Produkt 1

HCID 59452822
N-(2,6-difluorophenyl)-3-{3-[2-({2-(ethyloxy)-4-[4-(1-methylethyl)-1-piperazinyl]phenyl}amino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-2-yl}benzamide
Ausbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 64092,2,2-TrifluoroethanolLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
175 °C

Versuchsvorschrift

To 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-benzamide (Intermediate Example 1) (100 mg, 0.22 mmol) and {2-(ethyloxy)-4-[4-(1-methylethyl)-1-piperazinyl]phenyl}amine (57 mg, 0.22 mmol) in 2,2,2-trifluoroethanol (1.1 mL) was added 4 M HCl in dioxane (108 μL, 0.43 mmol). The mixture was stirred and heated on a Biotage microwave at 175° C. for 30 min, then cooled to rt. The mixture was neutralized with 0.5M sodium methoxide in MeOH. The mixture was concentrated under vacuum and the residue purified by silica gel chromatography to give a yellow oil. The oil was dissolved in minimal DCM, then hexane was added until a precipitate was formed. The slurry was cooled at −10° C. for 30 min, then poured through a Teflon filter, washing the solids with cold hexanes. The solids were dried under vacuum to give the title compound (98 mg, 0.14 mmol, 66%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.24 (s, 1H), 9.38 (brs, 1H), 8.36 (d, 2H, J=14.66 Hz), 8.23 (d, 1H, J=5.13 Hz), 8.05 (d, 1H, J=7.88 Hz), 7.81 (d, 1H, J=7.88 Hz), 7.73 (d, 1H, J=9.16 Hz), 7.61 (t, 1H, J=7.70 Hz), 7.36-7.49 (m, 3H), 7.21 (t, 2H, J=8.06 Hz), 6.97 (t, 1H, J=6.87 Hz), 6.65 (s, 1H), 6.45-6.50 (m, 2H), 4.06 (q, 2H, J=7.03 Hz), 3.08-3.14 (m, 4H), 2.64-2.69 (m, 1H), 2.54-2.61 (m, 4H), 1.24 (t, 3H, J=6.96 Hz), 1.00 (d, 6H, J=6.23 Hz). MS (ESI): 689 [M+H]+.

Aufarbeitung

  1. temperaturecooled to rt
  2. concentrationThe mixture was concentrated under vacuum
  3. customthe residue purified by silica gel chromatography
  4. customto give a yellow oil
  5. customwas formed
  6. temperatureThe slurry was cooled at −10° C. for 30 min
  7. filtrationfilter
  8. washwashing the solids with cold hexanes
  9. customThe solids were dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-334991e72e1e4c3e81c2a3533ff9706e
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08093239B2

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