Hydrochloric Acid → HCID 11512754, Verbindung

HRID 1159978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159978
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:33])[C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[NH2:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[CH2:40][CH:39]([NH:44][C:45](=O)C(F)(F)F)[CH2:38]2.Cl.[CH:52](O)(C)C>>[CH3:52][N:44]([CH3:45])[CH:39]1[CH2:38][C:37]2[C:41](=[CH:42][CH:43]=[C:35]([NH:34][C:2]3[N:7]=[C:6]([C:8]4[C:9]([C:17]5[CH:18]=[C:19]([NH:23][C:24](=[O:33])[C:25]6[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=6[F:32])[CH:20]=[CH:21][CH:22]=5)=[N:10][N:11]5[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=45)[CH:5]=[CH:4][N:3]=3)[CH:36]=2)[CH2:40]1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 59511384N-(5-amino-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamideHCID 59513803N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide

Produkt 1

HCID 11512754HCID 11512754, Verbindung

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

The title compound was synthesized by combining N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (200 mg, 0.43 mmol) (prepared according to a procedure similar to that described in Example 27, Step C), N-(5-amino-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide (127 mg, 0.52 mmol), hydrochloric acid (0.043 mmol, 43 μL 1M HCl/diethylether) and 2 mL isopropanol in a sealed vessel. The vial and contents were heated in a microwave synthesizer at 180° C. for 30 min. The reaction was cooled and concentrated. The residue was partitioned between EtOAc and saturated NaHCO3. The organic was washed with brine, dried with MgSO4 and concentrated. The crude material was purified by silica gel column chromatography (0-100% gradient; (90% DCM:9% MeOH:1% NH4OH/DCM)). Purification provided 278 mg (95%) of the coupled adduct. ESIMS (M+H)+=684.20.

Aufarbeitung

  1. customprepared
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between EtOAc and saturated NaHCO3
  5. washThe organic was washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel column chromatography (0-100% gradient; (90% DCM:9% MeOH:1% NH4OH/DCM))
  9. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-c9b3bdf7b0624bcf8f386933b0071919
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812022B2

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