Pyridine-2-carbonitrile → HCID 178439989, compound

HRID 1915560Notes

Reaction equation

HRID 1915560 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].[CH:26]([C:29]1[N:51]=[C:32]2[N:33]=[C:34]([C:43]3[CH:50]=[CH:49][C:46](C=O)=[CH:45][CH:44]=3)[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:36][N:31]2[N:30]=1)([CH3:28])[CH3:27].[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>[CH:26]([C:29]1[N:51]=[C:32]2[N:33]=[C:34]([C:43]3[CH:44]=[CH:45][C:46]([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:49][CH:50]=3)[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:36][N:31]2[N:30]=1)([CH3:28])[CH3:27]

Participants

9

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 86630671HCID 86630671, compound

Product 1

HCID 178439989HCID 178439989, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2.2 ml triethylamine is added to a solution of 1.90 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 140 ml methanol. To this solution a solution of 2.30 g 4-(2-isopropyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde in 140 ml DMF is added, followed by 2.4 ml glacial acetic acid and 3.0 g NaBH(OAc)3. The resulting mixture is stirred at room temperature. Four additional portions of 2 equivalents NaBH(OAc)3 are added after 2, 4, 5 and 8 hours. 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 product.

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])
  3. customto yield the product

Sources & evidence

ORD record
ord-16e88c0de33c41579fe4dbb2d20b4870
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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