Cyanoacetic acid → HCID 178461468, compound

HRID 1696227Notes

Reaction equation

HRID 1696227 reaction equation
Cl.Cl.[CH3:3][N:4]([C@@H:14]1[C@H:19]([CH3:20])[CH2:18][CH2:17][NH:16][CH2:15]1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:11][CH:12]=[N:13][C:6]=12.[C:21]([CH2:23][C:24](O)=[O:25])#[N:22].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C)C=O>[N:13]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH3:3])[C@@H:14]2[C@H:19]([CH3:20])[CH2:18][CH2:17][N:16]([C:24](=[O:25])[CH2:23][C:21]#[N:22])[CH2:15]2)[NH:11][CH:12]=1

Participants

6

Reactant 4

HCID 9740Cyanoacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178461466HCID 178461466, compound

Product 1

HCID 178461468HCID 178461468, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-3H-imidazo[4,5-b]pyridin-7-amine dihydrochloride (40 mg) in N,N-dimethylformamide (0.6 mL) were added cyanoacetic acid (16 mg), 1-hydroxybenzotriazole (25.5 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.033 mL). The mixture was stirred at ambient temperature overnight, then extracted with EtOAc and washed with brine. The extract was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 3-{(3R,4R)-3-[3H-imidazo[4,5-b]pyridin-7-yl(methyl)amino]-4-methyl-1-piperidinyl}-3-oxopropanenitrile (25 mg) as a white powder.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10)

Sources & evidence

ORD record
ord-98312fc2c0854b7290b011b57f2a7cc3
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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