Potassium Carbonate → HCID 68304833, compound

HRID 1190826Notes

Reaction equation

HRID 1190826 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]3[N:15]([CH3:28])[C:16](=[O:27])[N:17]([CH2:18][C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]#[N:22])[C:9]=23)[CH2:3]1.[C:29]([C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Br)#[N:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:29]([C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33][NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]3[N:15]([CH3:28])[C:16](=[O:27])[N:17]([CH2:18][C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]#[N:22])[C:9]=23)[CH2:3]1)#[N:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrileHCID 533110702-({7-[(3R)-3-Amino-1-piperidinyl]-3,5-dimethyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl}methyl)benzonitrile

Product 1

HCID 68304833HCID 68304833, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.1 g (R)-2-[[7-(3-aminopiperidin-1-yl)-3,5-dimethyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile (40.1 mmol) was added in a reaction bottle, to which 30 mL DMF was added. 8.6 g 2-cyano-benzyl bromide (44 mmol) and 11 g potassium carbonate (80 mmol) were added at 0° C. The reaction was continued for 3 h by stirring at room temperature. The reaction solution was extracted with dichloromethane, and washed with saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, and evaporated to dryness to afford 19.68 g crude product with a yield of 99.8%.

Workup

  1. additionwas added
  2. extractionThe reaction solution was extracted with dichloromethane
  3. washwashed with saturated sodium chloride solution
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-62b7ca53633c406ab23badc25d56d928
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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