Triethylamine → tert-butyl 2-(4-(3-methoxybenzamido)-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate

HRID 521609Notes

Reaction equation

[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([C:19]2[N:23]([CH3:24])[N:22]=[CH:21][CH:20]=2)[CH:3]=1.[C:25](Cl)(=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=1.C(N(CC)CC)C>ClCCl>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[C:25]([NH:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[C:4]([C:19]2[N:23]([CH3:24])[N:22]=[CH:21][CH:20]=2)[CH:3]=1)=[O:34]

Participants

Conditions

Temperature: 22 °C

Procedure

Tert-butyl 2-(4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate (265 mg, 797.2 μmol), m-anisoyl chloride (168.0 μl, 1.5 eq) and triethylamine (266.7 μl, 2.4 eq) were taken up in 20 mL of dichloromethane in a round bottomed flask and stirred at 22° C. for 18 hr. The reaction was then concentrated and purified by column chromatography (40-75% ethyl acetate in hexane) to afford the title compound as a pale yellow oil in 73.9% yield LCMS m/z (%)=467 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ ppm 1.43 (s, 9H), 3.42 (q, J=5.56 Hz, 2H), 3.78 (s, 3H), 3.88 (s, 3H), 4.04 (t, J=4.80 Hz, 2H), 6.28 (d, 1H), 7.01 (d, J=9.09 Hz, 1H), 7.10 (dt, J=4.55, 2.53 Hz, 1H), 7.38-7.41 (m, 2H), 7.43-7.45 (m, J=3.03 Hz, 1H), 7.54 (d, J=2.02 Hz, 1H), 7.66-7.71 (m, 1H), 7.76 (s, 1H).

Workup

concentrationThe reaction was then concentrated
custompurified by column chromatography (40-75% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-977f63b7db1844a18644f66694d05749
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328107B2

Reaction notes

Loading…