Hydrochloric Acid → HCID 16124788, compound

HRID 1945412Notes

Reaction equation

[CH3:1][NH:2][CH3:3].C[Al](C)C.C[O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH:18][C:19](=[O:38])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]34[CH2:37][CH:32]5[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]5)[CH2:29]3)[CH2:35]4)=[CH:24][CH:23]=2)[CH:12]=1.Cl>C1(C)C=CC=CC=1>[C:28]12([C:25]3[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:19]([NH:18][C:13]4[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=4[OH:17])[C:10]([N:2]([CH3:3])[CH3:1])=[O:9])=[O:38])=[CH:23][CH:24]=3)[CH2:35][CH:34]3[CH2:33][CH:32]([CH2:31][CH:30]([CH2:36]3)[CH2:29]1)[CH2:37]2

Participants

Conditions

Temperature: 80 °C

Procedure

Dimethyl amine (0.06 ml, 0.12 mmol) in anhydrous toluene 2 ml was treated with trimethyl aluminium (in 2.0 M Hexane, 0.15 ml, 0.31 mmol) under nitrogen. After 0.25 h, It was added 3-[2-(4-adamantan-1-yl-phenoxy)acetylamino]-4-hydroxy-benzoic acid methyl ester (30.1 mg, 0.07 mmol) in toluene 4 ml. The mixture was stirred for 3 h at 80° C. After cooling, the reaction mixture was treated with diluted HCl until no foaming more. The reaction mixture was separated with ethyl acetate and sodium bicarbonate. The organic phase was washed by brine, dried (MgSO4 anh), and concentrated. The residue was purified by preparative TLC(Hexane:EtoAC:MeOH=15:3:1) to give 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-N,N-dimethyl-benzamide as a white solid (10.4 mg, 23.2% yield).

Workup

temperatureAfter cooling
customThe reaction mixture was separated with ethyl acetate and sodium bicarbonate
washThe organic phase was washed by brine
dry with materialdried (MgSO4 anh)
concentrationconcentrated
customThe residue was purified by preparative TLC(Hexane:EtoAC:MeOH=15:3:1)

Sources & evidence

ORD record: ord-6b4b567dcead444885e4e4b3695b342f
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394799B2

Reaction notes

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