Pyridine-2-carbonitrile → HCID 178510327, Verbindung

HRID 1915535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1915535
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][N:12]3[C:21]([C:24]#[N:25])=[CH:22][N:23]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1)=O.[NH:26]([C:28]([CH:30]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]1)=O)[NH2:27].[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[C:49]#[N:50].[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:15]1([C:14]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:1][N:33]4[CH2:32][CH2:31][CH:30]([C:28]5[N:50]=[C:49]([C:44]6[CH:45]=[CH:46][CH:47]=[CH:48][N:43]=6)[NH:27][N:26]=5)[CH2:35][CH2:34]4)=[CH:4][CH:5]=3)=[N:10][C:11]3[N:12]([C:21]([C:24]#[N:25])=[CH:22][N:23]=3)[CH:13]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

9

Edukt 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 866306577-(4-Formylphenyl)-6-phenylimidazo[1,2-a]pyrimidine-3-carbonitrile

Produkt 1

HCID 178510327HCID 178510327, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

0.2 ml triethylamine is added to a solution of 260 mg of the product of step 1 in 5 ml methanol. To this solution a solution of 219 mg 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 5 ml DMF is added, followed by 0.091 ml glacial acetic acid and 127 mg NaBH(OAc)3. The resulting mixture is stirred at room temperature. Additional portions of 2 equivalents NaBH(OAc)3 are added after 1.5, 3 and 4 hours. The solvent is removed by evaporation after 6 h and the residue is purified by chromatography on silica gel (dichloromethane/methanol) to yield the desired compound.

Aufarbeitung

  1. customThe solvent is removed by evaporation after 6 h
  2. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-f1768cc241eb41e7b189e0bad9834e91
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614218B2

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