Triethylamine → 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79439

Reaktionsgleichung

Reaktionsgleichung von HRID 79439
[CH3:1][C:2]1([CH3:21])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]([OH:20])=O)=[CH:16][N:17]=[C:11]3[CH:10]=2)[CH2:4][O:3]1.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.C(N(CC)CC)C.[CH2:41]([C:43]1[C:51]2[C:50]([NH2:52])=[CH:49][CH:48]=[CH:47][C:46]=2[N:45]([CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([CH3:60])[N:55]=2)[N:44]=1)[CH3:42].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[CH3:21][C:2]1([CH3:1])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]([NH:52][C:50]4[CH:49]=[CH:48][CH:47]=[C:46]5[C:51]=4[C:43]([CH2:41][CH3:42])=[N:44][N:45]5[CH2:53][C:54]4[CH:59]=[CH:58][CH:57]=[C:56]([CH3:60])[N:55]=4)=[O:20])=[CH:16][N:17]=[C:11]3[CH:10]=2)[CH2:4][O:3]1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 672598043-ethyl-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amineHCID 672601837-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acid

Produkt 1

HCID 672594837-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideAusbeute 16,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred mixture of 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (128 mg, 0.44 mmol) in tetrahydrofuran (6 mL), under nitrogen, was added 2,4,6-trichlorobenzoyl chloride (115 mg, 0.47 mmol) and triethylamine (51 mg, 0.51 mmol). The mixture was stirred for 30 minutes. To the reaction mixture was added 3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (90 mg, 0.34 mmol), followed by lithium bis(trimethylsilyl)amide (1.7 mL, 1.7 mmol; 1M solution in tetrahydrofuran). The mixture was concentrated under reduced pressure and purified by flash chromatography on silica, eluting with dichloromethane/methanol (10:1) to give 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (30 mg).

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified by flash chromatography on silica
  3. washeluting with dichloromethane/methanol (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-cfe31da9445f4dc0b44f22515a3a8b99
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

Verknüpfte Notizen

Wird geladen…