Hydrochloric Acid → 6-{4-[({5-[(2-Fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-piperidin-1-yl}nicotinic acid

HRID 1713771Notes

Reaction equation

HRID 1713771 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[O:15][C:14]([C:16]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][N:26]=3)[CH2:21][CH2:20]2)=[O:17])=[N:13][N:12]=1.Cl>CO>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[O:15][C:14]([C:16]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:34]=[CH:33][C:28]([C:29]([OH:31])=[O:30])=[CH:27][N:26]=3)[CH2:21][CH2:20]2)=[O:17])=[N:13][N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59464313Methyl 6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-piperidin-1-yl}nicotinate

Product 1

HCID 594641666-{4-[({5-[(2-Fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-piperidin-1-yl}nicotinic acidYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2M NaOH (2 mL, 4 mmol) and methyl 6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}nicotinate (17 mg, 0.04 mmol) (Example 612) in MeOH (10 mL) was stirred for 16 h then taken to pH 7 by addition of 2M HCl. The solution was concentrated by evaporation to give a cloudy aqueous mixture that was cooled on an ice bath. The precipitate was collected by filtration, washed with water and Et2O and dried to give the title compound (13 mg, 88%) as a solid; 1H NMR (CD3OD) δ 8.61 (s, 1H), 8.02-7.88 (m, 2H), 7.16-7.05 (m, 2H), 7.05-6.97 (m, 1H), 6.75 (d, 1H), 4.47-4.37 (m, 2H), 4.17-4.06 (m, 1H), 3.08-2.97 (m, 2H), 1.99-1.89 (m, 2H), 1.63-1.50 (m, 2H); MS m/e MH+ 427.

Workup

  1. concentrationThe solution was concentrated by evaporation
  2. customto give a cloudy aqueous mixture that
  3. temperaturewas cooled on an ice bath
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water and Et2O
  6. customdried

Sources & evidence

ORD record
ord-d6e6c24e6fb74831a868476d50470c8d
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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