Hydrochloric Acid → HCID 10769547, compound

HRID 1604551Notes

Reaction equation

[Cl:1][C:2]1[C:20]([N:21]([C:23](=[O:41])[CH2:24][NH:25][C:26](=[O:40])/[CH:27]=[CH:28]/[C:29]2[CH:30]=[N:31][C:32]([C:35]([O:37]CC)=[O:36])=[CH:33][CH:34]=2)[CH3:22])=[CH:19][CH:18]=[C:17]([Cl:42])[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]=[CH:11]2.[OH-].[Na+].Cl>C(O)C>[C:35]([C:32]1[N:31]=[CH:30][C:29](/[CH:28]=[CH:27]/[C:26]([NH:25][CH2:24][C:23]([N:21]([C:20]2[C:2]([Cl:1])=[C:3]([C:17]([Cl:42])=[CH:18][CH:19]=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]=[CH:11]3)[CH3:22])=[O:41])=[O:40])=[CH:34][CH:33]=1)([OH:37])=[O:36]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 8-[2,6-dichloro-3-[N-[(E)-3-(6-ethoxycarbonylpyridin-3-yl)acryloylglycyl]-N-methylamino]benzyloxy]-2-methylquinoline (2.07 g) in ethanol (20 ml) was added 1N sodium hydroxide solution (3.75 ml) at ambient temperature. The mixture was stirred for 3 hours at 60° C. The reaction mixture was adjusted to pH 4 with 1N hydrochloric acid and concentrated. The residue was purified by flash chromatography (dichloromethane--methanol) to give 8-[3-[N-[(E)-3-(6-carboxypyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (1.71 g) as an amorphous powder.

Workup

concentrationconcentrated
customThe residue was purified by flash chromatography (dichloromethane--methanol)

Sources & evidence

ORD record: ord-858fd2f33f9048fcbb085b27d980217a
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994368

Reaction notes

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