Pyridine-2-carbonitrile → HCID 178419469, compound

HRID 1915566Notes

Reaction equation

HRID 1915566 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].[Br:26][C:27]1[CH:28]=[N:29][N:30]2[CH:35]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:33]([C:42]3[CH:49]=[CH:48][C:45](C=O)=[CH:44][CH:43]=3)=[N:32][C:31]=12.[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>[Br:26][C:27]1[CH:28]=[N:29][N:30]2[CH:35]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:33]([C:42]3[CH:43]=[CH:44][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:48][CH:49]=3)=[N:32][C:31]=12

Participants

9

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 86630675HCID 86630675, compound

Product 1

HCID 178419469HCID 178419469, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.29 ml triethylamine is added to a solution of 0.33 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 10 ml methanol. To this solution a solution of 0.34 g 4-(3-Bromo-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde in 10 ml DMF is added, followed by 0.14 ml glacial acetic acid and 0.38 g NaBH(OAc)3. The resulting mixture is stirred at room temperature. Fife additional portions of 2 equivalents NaBH(OAc)3 are added every 2 hours. The solvent is removed by evaporation after 24 h and the residue is purified by chromatography on silica gel (dichloromethane/methanol]). The purified product is suspended in methanol and collected by filtration.

Workup

  1. customThe solvent is removed by evaporation after 24 h
  2. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol])
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9950306567294e6e94113908b6e0c02b
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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