Bis(2-pyridylmethyl)amine → HCID 67404464, compound

HRID 910249

Reaction equation

HRID 910249 reaction equation
[N:1]1[C:2]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[CH:19][N:18]([CH2:21][C:22](O)=[O:23])[N:17]=3)=[CH:12][CH:11]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:25]1[CH:30]=[C:29]([CH2:31][NH:32][CH2:33][C:34]2[N:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:28]=[CH:27][CH:26]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[N:28]1[CH:27]=[CH:26][CH:25]=[CH:30][C:29]=1[CH2:31][N:32]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][N:39]=1)[C:22](=[O:23])[CH2:21][N:18]1[CH:19]=[CH:20][C:16]([C:13]2[CH:12]=[CH:11][C:10]([C:2]3[N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][N:4]4[CH:3]=3)=[CH:15][CH:14]=2)=[N:17]1

Participants

8

Reactant 4

HCID 73759Bis(2-pyridylmethyl)amineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67405489HCID 67405489, compound

Product 1

HCID 67404464HCID 67404464, compoundYield 72.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-[3-(4-Imidazo[1,2-a]pyridin-2-ylphenyl)-1H-1-pyrazolyl]acetic acid (51 mg), 2,2′-dipicolylamine (32 mg), and 1-hydroxybenzotriazole (27 mg) were dissolved in N,N-dimethylformamide (1 mL), and triethylamine (56 μL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38 mg) were added to the solution, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with chloroform and then drying over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to flash column chromatography. Fractions eluted by dichloromethane-methanol (20:1) were concentrated under reduced pressure, and the solid was recovered through filtration by use of diethyl ether, to thereby yield the title compound (58 mg).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialdrying over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. washFractions eluted by dichloromethane-methanol (20:1)
  5. concentrationwere concentrated under reduced pressure
  6. filtrationthe solid was recovered through filtration by use of diethyl ether

Sources & evidence

ORD record
ord-f9236efd8d384e90a53a9a1fa0931a3f
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Linked notes

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