Pyridine-2-carbonitrile → HCID 178435853, compound

HRID 1915552Notes

Reaction equation

HRID 1915552 reaction equation
[NH:1]([C:3]([CH:5]1[CH2:10][CH2:9][N:8](C(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[CH:27]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[C:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:39][N:38]3[CH:47]=[CH:48][N:49]=[C:37]3[N:36]=2)=[CH:31][CH:30]=1)[CH3:28]>CN(C=O)C.CO>[C:41]1([C:40]2[C:35]([C:32]3[CH:33]=[CH:34][C:29]([CH:27]([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)[CH3:28])=[CH:30][CH:31]=3)=[N:36][C:37]3[N:38]([CH:47]=[CH:48][N:49]=3)[CH:39]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 3

HCID 7522Pyridine-2-carbonitrileHCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 684610867-[4-(1-Bromoethyl)phenyl]-6-phenylimidazo[1,2-a]pyrimidine

Product 1

HCID 178435853HCID 178435853, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.2 g 2-(5-Piperidin-[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 7 ml DMF are added 120 mg of the product obtained in step 2 dissolved in 1 ml methanol and the mixture is stirred for 20 h. The mixture is concentrated and the crude product is purified by reversed phase HPLC (Water, 10 mM NH4COOH, pH 3.7/ACN)

Workup

  1. concentrationThe mixture is concentrated
  2. customthe crude product is purified by reversed phase HPLC (Water, 10 mM NH4COOH, pH 3.7/ACN)

Sources & evidence

ORD record
ord-798ad4665b5e4a1296e78ac13e4e7652
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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