Pyridine-2-carbonitrile → HCID 178432371, compound

HRID 1915580Notes

Reaction equation

HRID 1915580 reaction equation
[NH:1]([C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11](OC(C)(C)C)=O)[CH2:7][CH2:6]1)=O)[NH2:2].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]#[N:25].[CH3:26][C:27]1[N:50]=[C:30]2[N:31]=[C:32]([C:42]3[CH:49]=[CH:48][C:45](C=O)=[CH:44][CH:43]=3)[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[C:34]([CH3:35])[N:29]2[N:28]=1.[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>[CH3:26][C:27]1[N:50]=[C:30]2[N:31]=[C:32]([C:42]3[CH:49]=[CH:48][C:45]([CH2:11][N:8]4[CH2:7][CH2:6][CH:5]([C:3]5[N:25]=[C:24]([C:19]6[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=6)[NH:2][N:1]=5)[CH2:10][CH2:9]4)=[CH:44][CH:43]=3)[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[C:34]([CH3:35])[N:29]2[N:28]=1

Participants

9

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 86630684HCID 86630684, compound

Product 1

HCID 178432371HCID 178432371, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.49 ml triethylamine is added to a solution of 0.55 g 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 15 ml methanol. To this solution a solution of 0.50 g 4-(2,7-dimethyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde in 15 ml DMF is added, followed by 0.23 ml glacial acetic acid and 0.64 g NaBH(OAc)3. The resulting mixture is stirred at room temperature. Additional portions of 2 equivalents NaBH(OAc)3 are added after 1, 2, 3, 5 and 7 h. The solvent is removed by evaporation after 20 h and the residue is purified by chromatography on silica gel (dichloromethane/[dichloromethane+7M NH3 in methanol]) to yield the desired compound.

Workup

  1. customThe solvent is removed by evaporation after 20 h
  2. customthe residue is purified by chromatography on silica gel (dichloromethane/[dichloromethane+7M NH3 in methanol])

Sources & evidence

ORD record
ord-0bdc57ef5cd7439f88475f00cdfc4ef7
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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