Pyridine-2-carbonitrile → HCID 178504189, compound

HRID 1915568Notes

Reaction equation

HRID 1915568 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].[C:26]1([C:32]2[C:33]([C:47]3[CH:54]=[CH:53][C:50](C=O)=[CH:49][CH:48]=3)=[N:34][C:35]3[N:36]([N:38]=[CH:39][C:40]=3[C:41]#[C:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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>[C:26]1([C:32]2[C:33]([C:47]3[CH:48]=[CH:49][C:50]([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:53][CH:54]=3)=[N:34][C:35]3[N:36]([N:38]=[CH:39][C:40]=3[C:41]#[C:42][Si:43]([CH3:44])([CH3:45])[CH3:46])[CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

9

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 86630677HCID 86630677, compound

Product 1

HCID 178504189HCID 178504189, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.26 ml triethylamine is added to a solution of 0.30 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 0.33 g 4-{6-phenyl-3-[(trimethylsilyl)ethynyl]pyrazolo[1,5-a]pyrimidin-5-yl}benzaldehyde in 10 ml DMF is added, followed by 0.12 ml glacial acetic acid and 0.35 g NaBH(OAc)3. The resulting mixture is stirred at room temperature. Additional portions of 2 equivalents NaBH(OAc)3 are added after 1.5, 3, 6 and 8 hours. The solvent is removed by evaporation after 22 h and the residue is purified by chromatography on silica gel (dichloromethane/methanol) to yield the desired compound.

Workup

  1. customThe solvent is removed by evaporation after 22 h
  2. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-4853574d842c476fb0f42441915741e1
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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