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 1915529Notes

Reaction equation

HRID 1915529 reaction equation
[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

Participants

9

Reactant 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

Product 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

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

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.

Sources & evidence

ORD record
ord-3c26c67be31a458a81406284b907b508
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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