1,3-Dimethyl-2-imidazolidinone → HCID 67277927, Verbindung

HRID 1696231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696231
Cl[C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=[C:4]2[NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:13][C:3]=12.Cl.[CH3:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]1[NH2:29].C(N(CC)C(C)C)(C)C.CN1CCN(C)C1=O>CCOC(C)=O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[NH:11][C:4]3=[N:5][CH:6]=[C:7]([C:8]([NH2:10])=[O:9])[C:2]([NH:29][C@H:24]4[CH2:25][CH2:26][CH2:27][CH2:28][C@H:23]4[CH3:22])=[C:3]3[CH:13]=2)=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 81531DiisopropylethylamineHCID 119839064-Chloro-2-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamideHCID 672780792-Methylcyclohexylamine hydrochloride, (1S,2R)-

Produkt 1

HCID 67277927HCID 67277927, VerbindungAusbeute 15,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Chloro-2-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (70 mg),(1S,2R)-2-methylcyclohexanamine hydrochloride (108.5 mg),N,N-diisopropylethylamine (0.126 ml) and 1,3-dimethyl-2-imidazolidinone (0.35 ml) were combined and irradiated microwave at 16° C. for 1 hour. After cooled to ambient temperature, the mixture was diluted in EtOAc. The organic solution was washed with saturated aqueous sodium hydrogencarbonate, dried over MgSO4 and evaporated in vacuo. The residue was purified by preparative NH2 silica gel column chromatography with 5% methanol in chloroform to give 2-(4-fluorophenyl)-4-{[(1S,2R)-2-methylcyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (13.7 mg) as an off-white solid.

Aufarbeitung

  1. customirradiated microwave at 16° C. for 1 hour
  2. washThe organic solution was washed with saturated aqueous sodium hydrogencarbonate
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative NH2 silica gel column chromatography with 5% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-287af73f70f647a7a0f9a8102448cc02
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163767B2

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