Diisopropylethylamine → N-{5-bromo-2-[(pyridin-2-ylcarbonyl)amino]benzyl}pyridine-2-carboxamide

HRID 1786776Notes

Reaction equation

HRID 1786776 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:12].C(N(CC)C(C)C)(C)C.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](Cl)=[O:35]>C(Cl)Cl>[Br:9][C:7]1[CH:6]=[CH:5][C:4]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:12])=[C:3]([CH:8]=1)[CH2:2][NH:1][C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=1)=[O:35]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 57598296N-[2-(aminomethyl)-4-bromophenyl]pyridine-2-carboxamide

Product 1

HCID 11212049N-{5-bromo-2-[(pyridin-2-ylcarbonyl)amino]benzyl}pyridine-2-carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 2-3 (0.050 g, 0.16 mmoles) was dissolved in 6 mL of methylene chloride. To the reaction vessel was added (0.06 mL, 0.32 mmoles) of N,N-diisopropylethylamine and (200 mg, 0.32 mmols, 1.49 mmol/gram) followed by the addition of (0.057 g, 0.32 mmol) picolinoyl chloride. The mixture was stirred until complete by TLC. The compound was then filtered and then the solvent was removed and then purified on a mass guided LC/MS to provide 46 mg (70%) of the title compound. 1H NMR (300 MHz, CDCl3): 8.89 ppm (s, 2H), 8.43 ppm (m, 2H), 8.22 ppm (m, 2H), 8.13 ppm (t, J=4 Hz, 1H), 8.0 ppm (s, 1H), 7.81 ppm (m, 2H), 7.41 ppm (m, 1H), 7.2 ppm (m, 2H), 4.22 ppm (d, J=4 Hz, 2H); HRMS calc'd for C19H15BrN4O2 (M+1) 411.0451; Found: 411.0444

Workup

  1. filtrationThe compound was then filtered
  2. customthe solvent was removed
  3. custompurified on a mass

Sources & evidence

ORD record
ord-583ff380a4bf48fc946d55bf26c23e13
Source dataset
uspto-grants-2009_03
Patent number
US07507836B2

Reaction notes

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