Hydrochloric Acid → HCID 49839565, compound

HRID 449892Notes

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=2)[CH:8]=1)=[O:5].[Li+].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[CH:8]=1)=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 4-(4-(2,6-dichlorobenzamido)pyridin-2-ylamino)benzoate (500 mg, 1.2 mmol) in THF (30 mL) was added 2 N LiOH solution (2 mL, 1.5 mmol) dropwise. The reaction mixture was then stirred at 60° C. overnight. After cooling to room temperature, the reaction mixture was adjusted to pH=3-4 using HCl (2N, 2 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concenrated under reduced pressure. The residue was purified by silica gel column chromatography (MeOH/CH2Cl2: 1/10) to afford desired product (440 mg, yield: 94%). 1H NMR (400 MHz, DMSO) δ 12.36 (s, 1H), 11.01 (s, 1H), 9.55 (s, 1H), 8.14 (d, J=5.7, 1H), 7.90-7.73 (m, 5H), 7.67-7.43 (m, 5H), 6.91 (dd, J=5.7, 1.6, 1H). LCMS (ESI) m/z: 403.4 [M+H+].

Workup

temperatureAfter cooling to room temperature
extractionThe mixture was extracted with EtOAc (3×50 mL)
washThe combined organic extracts were washed with brine
dry with materialdried over MgSO4
customThe residue was purified by silica gel column chromatography (MeOH/CH2Cl2: 1/10)

Sources & evidence

ORD record: ord-33114bed5acf422eb2dbc97c93299241
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486950B2

Reaction notes

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