Sodium Hydroxide → HCID 23292016, compound

HRID 850184Notes

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-392a9df21cb248989e2150c8a855acf3
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015818

Reaction notes

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