Triethylamine → HCID 178424645, Verbindung

HRID 1851287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851287
[NH:1]1[CH2:4][CH:3]([C:5]2[NH:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=3)[N:6]=2)[CH2:2]1.C([N:19]([CH2:22]C)[CH2:20][CH3:21])C.C1([C:27]2[CH:34]=[C:33]([C:35]3[C:40]([C:41]4[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=4)=[CH:39][N:38]4[N:48]=CN=C4[N:36]=3)[CH:32]=[CH:31][C:28]=2[CH:29]=O)CC1.[BH-](OC(C)=O)(OC(C)=O)O[C:53]([CH3:55])=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C>[CH:21]1([C:20]2[N:19]=[C:22]3[N:36]=[C:35]([C:33]4[CH:34]=[CH:27][C:28]([CH2:29][N:1]5[CH2:4][CH:3]([C:5]6[N:6]=[C:7]([C:10]7[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=7)[NH:8][N:9]=6)[CH2:2]5)=[CH:31][CH:32]=4)[C:40]([C:41]4[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=4)=[CH:39][N:38]3[N:48]=2)[CH2:55][CH2:53]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 687534852-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridineHCID 867030522-Cyclopropyl-4-[6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde

Produkt 1

HCID 178424645HCID 178424645, VerbindungAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

164.5 mg 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine×2HCl (60% pure) are dissolved in 4.2 mL NMP. After addition of 0.16 mL triethylamine the reaction mixture is stirred for one hour. 350 mg 2-cyclopropyl-4-[6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde (50% pure) and 0.05 mL acetic acid are added. The reaction mixture is stirred overnight at room temperature. 113.8 mg (0.54 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 18 hours. After the usual work-up and chromatography 167 mg (58.3%) of the desired product are obtained.

Aufarbeitung

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-f65bfb8561a444c698cfed32a32afd99
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957064B2

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