Ethanolamine → HCID 57558171, compound

HRID 1162934Notes

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.C(O)C.Cl[CH2:16][C:17]([NH:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[C:25]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]([F:40])([F:39])[F:38])[NH:26][C:27]2=[O:30])=[CH:22][CH:21]=1)=[O:18]>O>[OH:2][CH2:1][CH2:3][NH:4][CH2:16][C:17]([NH:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[C:25]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]([F:40])([F:38])[F:39])[NH:26][C:27]2=[O:30])=[CH:22][CH:21]=1)=[O:18]

Participants

Conditions

Temperature: 70 °C

Procedure

Ethanolamine (22 μl, 0.368 mmol) and triethylamine (128 μl) were added to an ethanol solution (2 ml) that contained the 2-chloro-N-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]acetamide (70 mg, 0.184 mmol) obtained in step A. The obtained mixture was stirred at 70° C. for 18 hours. Thereafter, water was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The extract was washed with water and a saturated saline solution, and was then dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1), so as to obtain 2-(2-hydroxyethylamino)-N-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]acetamide (19 mg, 26%).

Workup

extractionthe mixture was then extracted with ethyl acetate
washThe extract was washed with water
dry with materiala saturated saline solution, and was then dried over anhydrous sodium sulfate
distillationThereafter, the solvent was distilled away under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1)

Sources & evidence

ORD record: ord-a0f97a35790e479b84077c2c2a771db9
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820693B2

Reaction notes

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