Nicotinic Acid → HCID 70570583, compound

HRID 2403579Notes

Reaction equation

HRID 2403579 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]([CH3:27])[C:16](=[O:26])[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=2)=[CH:4][CH:3]=1.[C:28](O)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH3:27][N:15]([CH2:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:28]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)=[O:35])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1)[C:16](=[O:26])[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22]

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70570127HCID 70570127, compound

Product 1

HCID 70570583HCID 70570583, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

tert-Butyl (2-{[(4′-aminobiphenyl-3-yl)methyl](methyl)amino}-2-oxoethyl)carbamate (300 mg) was dissolved in DMF (6 ml), and nicotinic acid (150 mg), WSC hydrochloride (233 mg), and HOBt (165 mg) were added thereto, followed by stirring at room temperature for 20 hours. Water was added thereto, followed by extraction with EtOAc. The organic layer was dried over MgSO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH=20/1) to obtain tert-butyl {2-[methyl({4′-[(pyridin-3-ylcarbonyl)amino]biphenyl-3-yl}methyl)amino]-2-oxoethyl}carbamate (328 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH=20/1)

Sources & evidence

ORD record
ord-de1a4bd5d6e44aa981ca3fd5127e39d7
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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