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Sodium borohydride → {3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-methanol

HRID 226047
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 226047
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[C:25]([CH:26]=[O:27])[C:20]4=[N:19][C:18]=3[CH3:28])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[C:25]([CH2:26][OH:27])[C:20]4=[N:19][C:18]=3[CH3:28])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]
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Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 577525973-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridine-8-carboxaldehyde

Produkt 1

HCID 57752721{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-methanolAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 3-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridine-8-carboxaldehyde (0.33 g, 0.89 mmol) in CH3OH 910 ml) is treated with NaBH4 (37 mg, 0.98 mmol), and stirred at RT for 30 min. It is quenched with sat. NH4Cl (5 mL), the organic solvent is removed in vacuo, and the residue is diluted with H2O (10 mL) ppm. The aqueous layer is extracted with EtOAC (2×30 mL); the combined organic layers is dried with Na2SO4; filtered and concentrated to give the title compound (0.29 g, 0.78 mmol, 87%). 1H NMR (CDCl3): δ. 0.90 (t, J=7.0 Hz, 3H), 0.91 (t, J=7.0 Hz, 3H), 1.78-1.98 (m, 4H), 2.42 (s, 3H), 2.43 (s, 3H), 2.45 (s, 3H), 3.36-3.42 (m, 1H), 4.39 (bs, 1H), 5.11 (s, 2H), 6.73 (d, J=5.7 Hz, 1H), 6.73 (s, 1H), 7.17 (d, J=6.6 Hz, 1H), 7.46 (d, J=6.6 Hz, 1H) ppm. ES-MS (m/z): calcd for C22H27N5O (M+H)+: 378.5. found: 378.3.

Aufarbeitung

  1. customIt is quenched with sat. NH4Cl (5 mL)
  2. customthe organic solvent is removed in vacuo
  3. additionthe residue is diluted with H2O (10 mL) ppm
  4. extractionThe aqueous layer is extracted with EtOAC (2×30 mL)
  5. dry with materialthe combined organic layers is dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4a009d3049004b9e9e5e29e8cf3c286f
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07557103B2

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