Sodium Hydroxide → HCID 23292016, compound

HRID 365568Notes

Reaction equation

[Cl:1][C:2]1[C:28]([N:29]([C:31](=[O:49])[CH2:32][NH:33][C:34](=[O:48])/[CH:35]=[CH:36]/[C:37]2[CH:38]=[N:39][C:40]([C:43]([O:45]CC)=[O:44])=[CH:41][CH:42]=2)[CH3:30])=[CH:27][CH:26]=[C:25]([Cl:50])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.[OH-].[Na+]>C(O)C>[C:43]([C:40]1[N:39]=[CH:38][C:37](/[CH:36]=[CH:35]/[C:34]([NH:33][CH2:32][C:31]([N:29]([C:28]2[C:2]([Cl:1])=[C:3]([C:25]([Cl:50])=[CH:26][CH:27]=2)[CH2:4][O:5][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:15]=2[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]3[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH3:30])=[O:49])=[O:48])=[CH:42][CH:41]=1)([OH:45])=[O:44]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-[2,6-dichloro-3-[N-[(E)-3-(6-ethoxycarbonylpyridin-3-yl)acryloylglycyl]-N-methylamino]benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline (30 mg) in ethanol (0.5 ml) was added 1N aqueous sodium hydroxide solution (0.1 ml) at ambient temperature, and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was evaporated in vacuo, and the residue was dissolved in water. The aqueous layer was washed with diethyl ether and adjusted to pH 5 with 1N hydrochloric acid. The precipitate was collected by filtration to give 8-[3-[N-[(E)-3-(6-carboxypyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline (28 mg) as powder.

Workup

customThe reaction mixture was evaporated in vacuo
dissolutionthe residue was dissolved in water
washThe aqueous layer was washed with diethyl ether
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-ad32a7c7d93341a1ada1532c9752b43a
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127389

Reaction notes

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