Acetic Acid → HCID 178429817, Verbindung

HRID 1851309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851309
[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]=[CH:12][N:11]=3)[N:6]=2)[CH2:2]1.C(N(CC)CC)C.[CH3:23][C:24]1[N:25]=[C:26]2[N:31]=[C:30]([C:32]3[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=3)[C:29]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:28]([NH:46][CH:47]([CH3:49])[CH3:48])[N:27]2[CH:50]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN1C(=O)CCC1>[CH:47]([NH:46][C:28]1[N:27]2[CH:50]=[C:24]([CH3:23])[N:25]=[C:26]2[N:31]=[C:30]([C:32]2[CH:39]=[CH:38][C:35]([CH2:36][N:1]3[CH2:4][CH:3]([C:5]4[N:6]=[C:7]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=5)[NH:8][N:9]=4)[CH2:2]3)=[CH:34][CH:33]=2)[C:29]=1[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([CH3:49])[CH3:48]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 687522842-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridineHCID 867030574-(2-Methyl-5-isopropylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde

Produkt 1

HCID 178429817HCID 178429817, VerbindungAusbeute 1,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

227.9 mg (0.83 mmol) 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 6.5 mL NMP. 0.25 mL (1.8 mmol) triethylamine are added and the reaction mixture is stirred for one hour. 280 mg (0.76 mmol) 4-(2-Methyl-5-isopropylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde and 0.08 mL (1.36 mmol) acetic acid are added. The reaction mixture is stirred for three days at room temperature. 176.2 mg (0.83 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 18 hours. Additional 88 mg NaBH(OAc)3 are added and stirring is continued for 26 hours. After the usual work-up and purification by column chromatography and by HPLC 4.9 mg (1.1%) of the desired title compound are obtained.

Aufarbeitung

  1. stirringThe reaction mixture is stirred for three days at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 18 hours
  3. stirringstirring
  4. waitis continued for 26 hours
  5. customAfter the usual work-up and purification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-48b27eda5dca4899b291006fb33aeae7
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957064B2

Notizen zur Reaktion

Wird geladen…