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

HRID 1713773Notes

Reaction equation

HRID 1713773 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[N:30]=[CH:29][C:28]([CH2:31][C:32]([O:34]C)=[O:33])=[CH:27][CH: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[CH2:20][CH2:21][N:22]([C:25]3[N:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][CH:26]=3)[CH2:23][CH2:24]2)=[O:17])=[N:13][N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59464268Methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}pyridin-3-yl)acetate2×

Product 1

HCID 59464036(6-{4-[({5-[(2-Fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-piperidin-1-yl}pyridin-3-yl)acetic acidYield 2.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2M NaOH (0.09 mL, 0.18 mmol) and methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}pyridin-3-yl)acetate (Intermediate 102) (41 mg, 0.09 mmol) in MeOH (1 mL) was stirred for 16 h then acidified with 2M HCl and concentrated by evaporation. The residue purified by preparative HPLC to give the title compound (1 mg) as a gum; 1H NMR (CD3OD) δ 1.78-1.63 (m, 3H), 2.11-2.00 (m, 2H), 3.35-3.25 (m, 2H), 3.55 (s, 2H), 4.23-4.07 (m, 3H), 7.07-6.99 (m, 1H), 7.15-7.07 (m, 2H), 7.30-7.23 (m, 1H), 7.79 (s, 1H), 7.89-7.83 (m, 1H), 7.99-7.91 (m, 1H); MS m/e MH+ 441.

Workup

  1. concentrationconcentrated by evaporation
  2. customThe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-5be833176beb409f8888d309527986a2
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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