Sodium Bicarbonate → Methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}-1-oxidopyridin-3-yl)acetate

HRID 1713878Notes

Reaction equation

HRID 1713878 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[N+:29]([O-:30])=[CH:28][C:27]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>CC(O)(CC)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[N+:29]([O-:30])=[CH:28][C:27]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:26][CH:25]=3)[CH2:21][CH2:22]2)=[O:15])=[N:11][N:10]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 59464117HCID 59464117, compoundHCID 594641305-[(2-fluorophenyl)amino]-N-piperidin-4-yl-1,3,4-oxadiazole-2-carboxamide2×

Product 1

HCID 59619585Methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}-1-oxidopyridin-3-yl)acetateYield 32.2%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

5-[(2-Fluorophenyl)amino]-N-piperidin-4-yl-1,3,4-oxadiazole-2-carboxamide (Intermediate 101) (100 mg, 0.33 mmol) and methyl (6-chloro-1-oxidopyridin-3-yl)acetate (67 mg, 0.33 mmol) were heated with sodium hydrogen carbonate (56 mg, 0.66 mmol) in 2-methyl-2-butanol (4 mL) at 100° C. for 22 h. The reaction mixture was concentrated by evaporation and the residue was dissolved in DMSO then filtered and purified by preparative HPLC to give the title compound (50 mg, 32%) as a gum; 1H NMR δ 1.94-1.74 (m, 4H), 2.58-2.43 (m, 2H), 2.95-2.84 (m, 2H), 3.65 (s, 3H), 4.07-3.93 (m, 3H), 7.21-7.12 (m, 2H), 7.35-7.23 (m, 2H), 7.45-7.40 (m, 1H), 8.06-7.98 (m, 1H), 8.25-8.20 (m, 1H), 9.13 (d, 1H), 10.64 (s, 1H); MS m/e MH+ 471.

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation
  2. dissolutionthe residue was dissolved in DMSO
  3. filtrationthen filtered
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b3ae287a4061430fad69a3356a529267
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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