Hydrochloric Acid → 4-[({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)methyl]benzoic acid

HRID 1293177Notes

Reaction equation

HRID 1293177 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=2)=[O:17])[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.O1CCCC1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:28][CH:29]=2)=[O:17])[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57572311Methyl 4-[({[5-chloro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)methyl]benzoate

Product 1

HCID 589053494-[({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)methyl]benzoic acidYield 66.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-[({[5-chloro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)methyl]benzoate (step 1, 154 mg, 0.37 mmol), tetrahydrofuran (2 mL), methanol (2 mL), and 2 N sodium hydroxide (2 mL) was stirred at room temperature for 4 h. The mixture was poured into 1N hydrochloric acid (30 mL), and extracted with ethyl acetate (50 mL). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by TLC [dichloromethane/ethyl acetate (1:2)] to give 98 mg (66%) of the title compound as white solids: 1H-NMR (DMSO-d6) δ 9.13 (1H, t, J=6.0 Hz), 8.29 (1H, dd, J=2.6, 1.5 Hz), 8.22 (1H, dd, J=2.6, 1.5 Hz), 7.88 (2H, d, J=8.1 Hz), 7.47 (2H, d, J=8.1 Hz), 7.29–7.26 (4H, m), 4.60 (2H, d, J=6.0 Hz); MS (ESI) m/z 401 (M+H)+, 399 (M−H)−.

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by TLC [dichloromethane/ethyl acetate (1:2)]

Sources & evidence

ORD record
ord-dc02a709dfe74659893493744cf511d4
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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