6-Chloronicotinamide → 6-{4-[({5-[(2-Fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-piperidin-1-yl}nicotinamide

HRID 1713772Notes

Reaction equation

HRID 1713772 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:15])=[N:11][N:10]=1.Cl[C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[CH:26][N:25]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][CH:17]2[CH2:18][CH2:19][N:20]([C:24]3[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[CH:26][N:25]=3)[CH2:21][CH2:22]2)=[O:15])=[N:11][N:10]=1

Participants

4

Reactant 2

HCID 804566-ChloronicotinamideHCID 594641305-[(2-fluorophenyl)amino]-N-piperidin-4-yl-1,3,4-oxadiazole-2-carboxamide2×

Product 1

HCID 594642836-{4-[({5-[(2-Fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-piperidin-1-yl}nicotinamideYield 2.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-[(2-fluorophenyl)amino]-N-piperidin-4-yl-1,3,4-oxadiazole-2-carboxamide (Intermediate 101) (200 mg, 0.66 mmol) and 6-chloronicotinamide (103 mg, 0.66 mmol) in dry DMF (4 mL) was heated in the microwave at 125° C. for 20 minutes and then for a further 10 minutes at 135° C. The mixture was filtered and purified by preparative HPLC to give the title compound (7 mg, 2.5%) as a solid; 1H NMR δ 1.55-1.65 (2H, m), 1.83-1.86 (2H, m), 2.99 (2H, t), 4.04-4.12 (1H, m), 4.42-4.46 (2H, m), 6.87 (1H, d), 7.11 (2H, m), 7.21-7.30 (2H, m), 7.72 (1H, s), 7.94-8.03 (2H, m), 8.62 (1H, d), 8.99 (1H, d), 10.61 (1H, s); MS m/e MH+ 426.

Workup

  1. filtrationThe mixture was filtered
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f8788030854442fda00208ad04405e12
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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