2-(Dimethylamino)ethanol → {2-[4-(3-Methoxy-benzoylamino)-2-(2-methyl-2H-pyrazol-3-yl)-phenoxy]-ethyl}-carbamic acid 2-dimethylamino-ethyl Ester

HRID 521616Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][CH:34]=1)[C:6]([NH:8][C:9]1[CH:25]=[CH:24][C:12]([O:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19](Cl)(Cl)Cl)=[C:11]([C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)[CH:10]=1)=[O:7].[CH3:35][N:36]([CH3:40])[CH2:37]CO.[O-2].[Mg+2]>C(OCC)(=O)C>[CH3:35][N:36]([CH3:40])[CH2:37][CH2:19][O:18][C:17](=[O:23])[NH:16][CH2:15][CH2:14][O:13][C:12]1[CH:24]=[CH:25][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:32]=[CH:33][CH:34]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:10][C:11]=1[C:26]1[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 22 °C

Procedure

Trichloromethyl 2-(4-(3-methoxybenzamido)-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate (50.0 g, 94.74 mmol), 2-(dimethylamino)ethanol (14.50 g, 1.1 eq) and magnesium oxide (1.067 mL, 1.0 eq) were taken up in 2 mL of ethyl acetate in a round bottomed flask and stirred at 22° C. for 3 hr. The magnesium oxide was filtered off. The solvent was then evaporated and it was purified by HPLC. The proper fractions were collected and lyophilized to afford the title compound as a white solid in 31.3% yield. LCMS m/z (%)=482 (M+H, 100). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.82 (s, 3H), 2.84 (s, 3H), 3.34 (q, J=5.05 Hz, 4H), 3.69 (s, 3H), 3.84 (s, 3H), 4.06 (t, J=5.56 Hz, 2H), 4.25-4.29 (m, 2H), 6.28 (d, J=1.52 Hz, 1H), 7.14-7.22 (m, 2H), 7.40 (t, J=5.56 Hz, 1H), 7.47 (d, J=2.02 Hz, 3H), 7.51-7.55 (m, 1H), 7.70 (d, J=2.53 Hz, 1H), 7.84 (dd, J=8.84, 2.78 Hz, 1H), 9.48-9.62 (m, 1H).

Workup

filtrationThe magnesium oxide was filtered off
customThe solvent was then evaporated
customit was purified by HPLC
customThe proper fractions were collected

Sources & evidence

ORD record: ord-1c14912622844c8bad2ebd76df5c090d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328107B2

Reaction notes

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