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

HRID 503751Notes

Reaction equation

HRID 503751 reaction equation
[CH3:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH:25]([C:27]([CH:29]1[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]1)=O)[NH2:26].[N:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[C:48]#[N:49].[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>[CH3:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([C:11]2[CH:18]=[CH:17][C:14]([CH2:15][N:32]3[CH2:31][CH2:30][CH:29]([C:27]4[N:49]=[C:48]([C:43]5[CH:44]=[CH:45][CH:46]=[CH:47][N:42]=5)[NH:26][N:25]=4)[CH2:34][CH2:33]3)=[CH:13][CH:12]=2)[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 866306684-(5-Methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 1784219095-methyl-6-phenyl-7-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)imidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.11 ml triethylamine is added to a solution of 105 mg of the product of step 3 in 5 ml methanol. To this solution a solution of 0.122 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 5 ml DMF is added, followed by 0.05 ml glacial acetic acid and 144 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, 6 and 7 hours.

Sources & evidence

ORD record
ord-8710da41d0f042eda67a20d181eeef4b
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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