Pyridine-2-carbonitrile → HCID 178496980, compound

HRID 503810Notes

Reaction equation

HRID 503810 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([C:28]1[CH:33]=[CH:32][C:31]([C:34]2[C:39]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:38][N:37]3[N:46]=[C:47]([C:49]([O:51][CH3:52])=[O:50])[CH:48]=[C:36]3[N:35]=2)=[CH:30][CH:29]=1)=O.[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:40]1([C:39]2[C:34]([C:31]3[CH:30]=[CH:29][C:28]([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:33][CH:32]=3)=[N:35][C:36]3[N:37]([N:46]=[C:47]([C:49]([O:51][CH3:52])=[O:50])[CH:48]=3)[CH:38]=2)[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

9

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 86630701HCID 86630701, compound

Product 1

HCID 178496980HCID 178496980, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.36 ml triethylamine is added to a solution of 406 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 15 ml methanol. To this solution a solution of 400 mg methyl 5-(4-formylphenyl)-6-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate in 15 ml DMF is added, followed by 0.17 ml glacial acetic acid and 473 mg NaBH(OAc)3. The resulting mixture is stirred at room temperature. Additional portions of 2 equivalents NaBH(OAc)3 are added after 1 and 2 hours. The solvent is removed by evaporation after 3 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 3 h
  2. customthe residue is purified by chromatography on silica gel (dichloromethane/[dichloromethane+7M NH3 in methanol])

Sources & evidence

ORD record
ord-2de8fa0b3f6b4a99866da678fc52c775
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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