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Lithium hexamethyldisilazane → N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(1-methyl-1H-pyrazol-5-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706632
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 706632
[CH3:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:30][N:31]1[C:35]([C:36]2[CH:41]=[CH:40][N:39]3[C:42]([C:45](OC)=[O:46])=[CH:43][N:44]=[C:38]3[CH:37]=2)=[CH:34][CH:33]=[N:32]1>C1COCC1.CO.C(Cl)Cl>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][C:45]([C:42]2[N:39]3[CH:40]=[CH:41][C:36]([C:35]4[N:31]([CH3:30])[N:32]=[CH:33][CH:34]=4)=[CH:37][C:38]3=[N:44][CH:43]=2)=[O:46])[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[N:3]=1
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Komponenten

6

Edukt 3

HCID 2733832Lithium hexamethyldisilazaneHCID 672609383-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amineHCID 86699332Methyl 7-(1-methyl-1H-pyrazol-5-yl)imidazo[1,2-a]pyridine-3-carboxylate

Produkt 1

HCID 57387409N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(1-methyl-1H-pyrazol-5-yl)imidazo[1,2-a]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To a solution of 3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (46.7 mg, 0.185 mmol) in anhydrous THF (2 ml) was added under a nitrogen atmosphere at ambient temperature lithium bis(trimethylsilyl)amide (1.0 M in THF, 0.38 mL). The resulting mixture was stirred at ambient temperature for 10 minutes, then added dropwise to a chilled (ice-water bath) solution of methyl 7-(1-methyl-1H-pyrazol-5-yl)imidazo[1,2-a]pyridine-3-carboxylate (47.4 mg, 0.185 mmol) in anhydrous THF (2 mL). The cold bath was removed, and the reaction mixture was allowed to warm to ambient temperature, and quenched with water. The resulting suspension was extracted with DCM. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford the dried product. The crude product was subjected to preparative thin-layer chromatography on silica with 8% MeOH/DCM as eluent to afford 45.7 mg of pure, desired product as a yellow-brown solid. MS (ES+APCI) m/z=477 (M+H) detected.

Aufarbeitung

  1. additionadded dropwise to
  2. customThe cold bath was removed
  3. temperatureto warm to ambient temperature
  4. customquenched with water
  5. extractionThe resulting suspension was extracted with DCM
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto afford the dried product

Quellen und Nachweise

ORD-Eintrag
ord-344acd67b65940bbaea8dbc58c5de54e
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09174981B2

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