Hydrochloric Acid → 6-[(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-nicotinic acid

HRID 1807547Notes

Reaction equation

HRID 1807547 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1.O.CO.C(OCC)C>[CH2:18]([C:13]1[C:12]([CH2:11][NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:22])=[O:2])=[CH:5][N:6]=2)=[C:16]([CH3:17])[O:15][N:14]=1)[CH2:19][CH2:20][CH3:21]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66643788Methyl 6-(((3-butyl-5-methylisoxazol-4-yl)methyl)amino)nicotinate

Product 1

HCID 666435846-[(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-nicotinic acidYield 87%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-[(3-butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-nicotinic acid methyl ester (1.09 g, 4.0 mmol) in THF (11 mL) was added a solution of lithium hydroxide monohydrate (302 mg, 7.0 mmol) in water (11 mL) and methanol (11 mL). The resulting mixture was stirred at room temperature overnight. The mixture was acidified to pH 4 with HCl (1 N) and the resulting mixture diluted with diethylether. The aqueous phase was removed and the organic phase triturated with hexane-diethylether to afford the title compound (910 mg, 87%) which was obtained as a white solid. MS: m/e=288.4 [M−H]−.

Workup

  1. customThe aqueous phase was removed
  2. customthe organic phase triturated with hexane-diethylether

Sources & evidence

ORD record
ord-25963a6a00be4610bf05b192dac79826
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

Loading…