Methyl 6-chloropyridine-3-carboxylate → Methyl 6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-piperidin-1-yl}nicotinate

HRID 1713770Notes

Reaction equation

HRID 1713770 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:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[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:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][N:25]=3)[CH2:21][CH2:22]2)=[O:15])=[N:11][N:10]=1

Participants

4

Reactant 2

HCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 594641305-[(2-fluorophenyl)amino]-N-piperidin-4-yl-1,3,4-oxadiazole-2-carboxamide2×

Product 1

HCID 59464313Methyl 6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-piperidin-1-yl}nicotinateYield 12%

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) (100 mg, 0.33 mmol) and methyl 6-chloronicotinate (56 mg, 0.33 mmol) in dry DMF (3 mL) was heated in the microwave at 120° C. for 1 h. The reaction mixture was filtered and the filtrate was purified by preparative HPLC to give the title compound (17 mg, 12%) as a solid; 1H NMR δ 1.66-1.53 (m, 2H), 1.92-1.82 (m, 2H), 3.12-2.99 (m, 2H), 3.80 (s, 3H), 4.16-4.04 (m, 1H), 4.54-4.42 (m, 2H), 6.92 (d, 1H), 7.18-7.10 (m, 1H), 7.33-7.21 (m, 2H), 7.97-7.92 (m, 1H), 8.04-7.98 (m, 1H), 8.65 (d, 1H), 9.03 (d, 1H), 10.62 (s, 1H); MS m/e MH+ 441.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-c39c2949b18642a1b2e2480328049424
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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