Pyridine-2-carbonitrile → HCID 178420109, compound

HRID 1915533Notes

Reaction equation

HRID 1915533 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]([N: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[N:48]=[C:47]([C:42]6[CH:43]=[CH:44][CH:45]=[CH:46][N:41]=6)[NH:25][N:24]=5)[CH2:33][CH2:32]4)=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([N: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 86630656HCID 86630656, compound

Product 1

HCID 178420109HCID 178420109, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.09 ml triethylamine is added to a solution of 80 mg 4-(6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde in 3 ml methanol. To this solution a solution of 97 mg 2-(5-Piperidin-4H[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 3 ml DMF is added, followed by 0.04 ml glacial acetic acid and 114 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 5 hours.

Sources & evidence

ORD record
ord-2a2784cea00f4b9eb8185291e80e835a
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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