Methanol → 1-[6-Chloro-5-[[(2-cyclohexylethyl)amino]carbonyl]-2-quinolinyl]-4-piperidinecarboxylic acid

HRID 2217879Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([Cl:33])[C:18]=3[C:22]([NH:24][CH2:25][CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:23])[N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.CO.[OH-].[K+]>O>[Cl:33][C:17]1[C:18]([C:22]([NH:24][CH2:25][CH2:26][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)=[O:23])=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([N:9]1[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]1)[CH:21]=[CH:20]2

Participants

Conditions

Temperature: 70 °C

Procedure

To a 10 mL vial was added 1-[6-chloro-5-[[(2-cyclohexylethyl)amino]carbonyl]-2-quinolinyl]-4-piperidinecarboxylic acid ethyl ester (Example 76(d)) (200 mg), methanol (2 mL) and potassium hydroxide (100 mg) in water (1 mL)). The vial was sealed and heated at 70° C. in a microwave for 10 minutes. The mixture was concentrated and the residue was acidified to pH 5 with aqueous 2 M hydrochloric acid. The resulting solid was collected by filtration. Purification (Varian NH2 cartridge using methanol:dichloromethane 1:1 (100 mL) and then 2% acetic acid in methanol:dichloromethane 1:1(100 mL) as eluant) afforded the title compound (150 mg).

Workup

customThe vial was sealed
concentrationThe mixture was concentrated
filtrationThe resulting solid was collected by filtration
customPurification (Varian NH2 cartridge

Sources & evidence

ORD record: ord-b32f9652d5fe434c937755296485f2b4
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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