Acetic Acid → HCID 178518684, Verbindung

HRID 605009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605009
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[NH:11][N:10]=2)[CH2:5][CH2:4]1.[O:20]=[C:21]1[C:30]2[N:29]=[C:28]([C:31]3[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=3)[C:27]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:26][C:25]=2[CH:24]=[CH:23][NH:22]1.C(N(CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.CO>[C:39]1([C:27]2[C:28]([C:31]3[CH:32]=[CH:33][C:34]([CH2:35][N:3]4[CH2:8][CH2:7][CH:6]([C:9]5[N:13]=[C:12]([C:14]6[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=6)[NH:11][N:10]=5)[CH2:5][CH2:4]4)=[CH:37][CH:38]=3)=[N:29][C:30]3[C:21](=[O:20])[NH:22][CH:23]=[CH:24][C:25]=3[CH:26]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59846152HCID 59846152, VerbindungHCID 1784785342-(5-Piperidin-4-yl-4h-1,2,4-triazol-3-yl)-pyridine dihydrochloride

Produkt 1

HCID 178518684HCID 178518684, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-piperidin-4-yl-1H-1,2,4-triazol-5-yl)pyridine dihydro-chloride (46 mg, 0.15 mmol) and 4-(8-oxo-3-phenyl-7,8-dihydro-1,7-naphthyridin-2-yl)benzaldehyde (40 mg, 0.12 mmol) in dry DMF (0.5 mL) was added triethylamine (55 μL, 0.40 mmol). After stirring for 10 minutes acetic acid (70 μL, 1.20 mmol) was added and the mixture was stirred at room temperature over night. Then sodium triacetoxy borohydride (52 mg, 0.24 mmol) was added in one portion. After two hours the reaction was complete and some methanol was added. This reaction mixture was concentrated to a smaller volume and adsorbed on silica gel and purified by column chromatography eluting with 0.5-13% methanol/ethyl acetate (sat'd NH3). The appropriate fractions were combined and the solvents removed in vacuo. The residue was triturated with diethyl ether to give pure title compound as a white solid. 1H NMR (500 MHz, DMSO-d6): δ 14.34 (1H, br s), 11.56 (1H, d, J=5.6 Hz), 8.68 (1H, br s), 8.15 (1H, s), 8.03 (1H, m), 7.96 (1H, m), 7.50 (1H, br s), 7.22-7-38 (10H, m), 6.62 (1H, d, J=6.8 Hz), 3.49 (2H, s), 2.84 (2H, brm), 2.69 (1H, m), 2.07 (2H, brt, J=11 Hz), 1.94 (2H, m), 1.78 (2H, m). m/e (m+1): 540.3, 270.8 [(m+2)/2].

Aufarbeitung

  1. additionwas added
  2. concentrationThis reaction mixture was concentrated to a smaller volume
  3. custompurified by column chromatography
  4. washeluting with 0.5-13% methanol/ethyl acetate (sat'd NH3)
  5. customthe solvents removed in vacuo
  6. customThe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9037820265ef48519a7ccc3bddba73ac
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910561B2

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