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Formaldehyde → 3-Butyl-4-(4-cyclohexyloxy-3-oxazol-2-yl-phenyl)-6-(1-methyl-piperidin-4-yloxy)-pyridazine

HRID 2168737
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2168737
Cl.Cl.[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:31][CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[C:15]([C:26]2[O:27][CH:28]=[CH:29][N:30]=2)[CH:14]=1)[CH2:4][CH2:5][CH3:6].C=O.[C:40](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCl.O.O.C(Cl)Cl.C(O)(=O)C>[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:31][CH:32]2[CH2:37][CH2:36][N:35]([CH3:40])[CH2:34][CH2:33]2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[C:15]([C:26]2[O:27][CH:28]=[CH:29][N:30]=2)[CH:14]=1)[CH2:4][CH2:5][CH3:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67374053HCID 67374053, Verbindung

Produkt 1

HCID 533720673-Butyl-4-(4-cyclohexyloxy-3-oxazol-2-yl-phenyl)-6-(1-methyl-piperidin-4-yloxy)-pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176
Acetic Acid
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

To a solution of 3-butyl-4-(4-cyclohexyloxy-3-oxazol-2-yl-phenyl)-6-(piperidin-4-yloxy)-pyridazine dihydrochloride (50 mg, 0.091 mmol) in dichloromethane (2.0 mL) was added formaldehyde solution in water (37%, 0.25 mL), and 0.1 mL of acetic acid. Then sodium triacetoxyborohydride (300 mg) was added. And the mixture was stirred at room temperature for 10 min then condensed. It was then diluted with water/DCM, neutralized with sat NaHCO3 powder, organic layer was separated washed with water, brine and dried (Na2SO4). The solvent was removed in vacuo and the residue was purified by column chromatography using 5% methanolic solution of ammonia (2.0 M ammonia in methanol) in DCM to get 3-butyl-4-(4-cyclohexyloxy-3-oxazol-2-yl-phenyl)-6-(1-methyl-piperidin-4-yloxy)-pyridazine. This compound was dissolved in DCM (2.0 mL) and 1.0 mL of 4.0 M HCl in dioxane was added. Solvents were evaporated resulting solid was washed with ether and dried to provide the title compound (25 mg). LCMS: m/z 492 [M+1].

Aufarbeitung

  1. customcondensed
  2. customwas separated
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-03543069cf804086978cf768258a2743
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09045461B2

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