Pyridine-2-carbonitrile → 6-Phenyl-7-(4-{[4-(3-pyridin-2-yl-1,2,4-triazol-5-yl)piperidin-1-yl]methyl}phenyl)imidazo[1,2-a]pyrimidine

HRID 503724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503724
[C:1]1([C:7]2[C:8]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([CH:13]=[CH:14][N:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:24]([C:26]([CH:28]1[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]1)=O)[NH2:25].[N:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[C:47]#[N:48].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.CN(C=O)C.C(O)(=O)C.C(N(CC)CC)C>[C:1]1([C:7]2[C:8]([C:16]3[CH:23]=[CH:22][C:19]([CH2:20][N:31]4[CH2:30][CH2:29][CH:28]([C:26]5[NH:24][N:25]=[C:47]([C:42]6[CH:43]=[CH:44][CH:45]=[CH:46][N:41]=6)[N:48]=5)[CH2:33][CH2:32]4)=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([CH:13]=[CH:14][N:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

9

Edukt 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 866306554-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Produkt 1

HCID 251896856-Phenyl-7-(4-{[4-(3-pyridin-2-yl-1,2,4-triazol-5-yl)piperidin-1-yl]methyl}phenyl)imidazo[1,2-a]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

0.55 ml triethylamine is added to a solution of 0.5 g 4-(6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde in 15 ml methanol. To this solution a solution of 0.6 g 2-(5-Piperidin-[1,2,4]triazol-3-yl)-pyridine*2HCl (prepared from tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate and pyridine-2-carbonitrile according to a procedure described in U.S. Pat. No. 4,011,218 or WO2005100344) in 15 ml DMF is added, followed by 0.25 ml glacial acetic acid and 700 mg NaBH(OAc)3. The resulting mixture is stirred at room temperature. Three additional portions of 2 equivalents NaBH(OAc)3 are added after 2, 4 and 20 hours.

Quellen und Nachweise

ORD-Eintrag
ord-d9c81fc37cf54a4c9cecb266c2220433
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776864B2

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