Pyridine-2-carbonitrile → HCID 178486596, compound

HRID 503758Notes

Reaction equation

HRID 503758 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][O:27][C:28]1[N:33]2[N:34]=[CH:35][CH:36]=[C:32]2[N:31]=[C:30]([C:37]2[CH:44]=[CH:43][C:40](C=O)=[CH:39][CH:38]=2)[C:29]=1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=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][O:27][C:28]1[N:33]2[N:34]=[CH:35][CH:36]=[C:32]2[N:31]=[C:30]([C:37]2[CH:44]=[CH:43][C:40]([CH2:11][N:8]3[CH2:7][CH2:6][CH:5]([C:3]4[N:25]=[C:24]([C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=5)[NH:2][N:1]=4)[CH2:10][CH2:9]3)=[CH:39][CH:38]=2)[C:29]=1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

9

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 866306734-(7-Methoxy-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Product 1

HCID 178486596HCID 178486596, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.32 ml triethylamine is added to a solution of 0.42 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 0.37 g 4-(7-methoxy-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde in 10 ml DMF is added, followed by 0.15 ml glacial acetic acid and 0.43 g NaBH(OAc)3. The resulting mixture is stirred at room temperature. Four additional portions of 2 equivalents NaBH(OAc)3 are added after 1, 2, 3 and 7 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-77ab15730f454c9d8e47dfe334ad3d79
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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