Hydrochloric Acid → HCID 71462558, compound

HRID 1430773Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

(E)-3-(3-(4-Adamantan-1-yl-phenoxy)acrylamido)benzoic acid (60 mg, 0.144 mmol) and 2-(dimethylamino)ethylchloride.HCl (31.1 mg, 0.216 mmol) were dissolved in DMF (3 ml), to which K2CO3 (39.8 mg, 0.288 mmol) was added, followed by stirring at 60° C. for 12 hours. The reaction mixture was extracted with ethylacetate and NaHCO3 solution, thereafter the organic layer was washed with NaCl solution and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by Prep-TLC (n-Hexane:EtOAc=10:1) to give the target compound as a white solid (21.5 mg, yield: 10.6%).

Workup

additionwas added
extractionThe reaction mixture was extracted with ethylacetate and NaHCO3 solution
washthe organic layer was washed with NaCl solution and water
dry with materialdried over anhydrous MgSO4
concentrationconcentrated
customThe residue was purified by Prep-TLC (n-Hexane:EtOAc=10:1)

Sources & evidence

ORD record: ord-fe952e73f5bb4e98a03479b85c0ff37c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940936B2

Reaction notes

Loading…