1-Hydroxybenzotriazole → 3-[(2-ethylpiperidin-1-yl)carbonyl]-N-(2-furylmethyl)-6-methylpyridin-2-amine

HRID 2192782Notes

Reaction equation

HRID 2192782 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[N:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[CH2:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]1)[CH3:19].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]1[C:10]([C:9]1[C:8]([NH:7][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[N:16][C:15]([CH3:17])=[CH:14][CH:13]=1)=[O:12])[CH3:19]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 942052-EthylpiperidineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 596252852-[(2-Furylmethyl)amino]-6-methylnicotinic acid

Product 1

HCID 596252363-[(2-ethylpiperidin-1-yl)carbonyl]-N-(2-furylmethyl)-6-methylpyridin-2-amineYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(2-furylmethyl)amino]-6-methylnicotinic acid (65.0 mg) and 2-ethylpiperidine (47.5 mg) in DMF (2.8 ml) were added HOBt (45.9 mg) and WSC.HCl (65.2 mg), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 2% aqueous sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (0:1-3:7) was concentrated under reduced pressure to give the object compound (81.8 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. washthe fraction eluted with ethyl acetate-hexane (0:1-3:7)
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f4e38732dc2498582545c252fea28ba
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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