Sodium Hydroxide → HCID 10579237, compound

HRID 1871120Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[(E)-3-(6-ethoxycarbonylpyridin-3-yl)acryloylaminomethyl]pyrrole (116 mg) in ethanol was added 1N sodium hydroxide solution (0.3 ml) at ambient temperatures, and the mixture was stirred at 50° C. for 2 hours. The solvent was removed in vacuo, and the residue was dissolved in water. The aqueous solution was washed with diethyl ether and adjusted to pH 5 with 1N hydrochloric acid. The resulting precipitates were collected by filtration and washed with water and diethyl ether to give 2-[(E)-3-(6-carboxypyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]pyrrole (77 mg) as amorphous powder.

Workup

customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in water
washThe aqueous solution was washed with diethyl ether
customThe resulting precipitates
filtrationwere collected by filtration
washwashed with water and diethyl ether

Sources & evidence

ORD record: ord-838991ef3c9f4ba7ad27866851a9c51f
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06100284

Reaction notes

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