Dimethylamine → (S)-2-(5-bromo-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate

HRID 931752Notes

Reaction equation

[Br:1][C:2]1[C:11]([C@H:12]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:13][O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[C:10]([CH3:26])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:28])=[N+:7]2[O-].C1(S(Cl)(=O)=O)C=CC=CC=1.[CH3:39][NH:40][CH3:41]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:15]([O:14][CH2:13][C@H:12]([C:11]1[C:2]([Br:1])=[C:3]2[C:8](=[CH:9][C:10]=1[CH3:26])[N:7]=[C:6]([CH2:28][N:40]([CH3:41])[CH3:39])[CH:5]=[CH:4]2)[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred solution of (S)-5-bromo-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-2,7-dimethylquinoline 1-oxide (25 mg, 0.055 mmol) in toluene (3 mL) was added benzenesulfonyl chloride (0.06 mL, 0.24 mmol). The mixture was stirred at 110° C. for 16 hours, then cooled to room temperature. Dimethylamine (2 mL 2 M solution in methanol, excess) was added. The mixture was stirred at room temperature for 16 h, then diluted in ethyl acetate (30 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by HPLC to provide the desired product as a white solid (11 mg, 42%). LCMS-ESI+ (m/z): 479.3, 481.3 (M+H)+.

Workup

temperaturecooled to room temperature
stirringThe mixture was stirred at room temperature for 16 h
washwashed with NaHCO3 solution, water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe obtained residue was purified by HPLC

Sources & evidence

ORD record: ord-ffd65dbbf9c44b4588fd9f7f996ea2c7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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