Réaction #2487484

Équation de réaction

intermediate 1

N-(3-(2-(4-(1-acetylazetidin-3-ylamino)-2-methoxyphenylamino)-5-(trifluoromethyl)pyrimidin-4-ylamino)phenyl)acrylamide

intermediate 1

N-(3-(2-(4-(1-(2-fluoroethyl)azetidin-3-ylamino)-2-methoxyphenylamino)-5-(trifluoromethyl)pyrimidin-4-ylamino)phenyl)acrylamide

trifluoroacetic acid

→

title compound

tert-butyl 3-(4-(4-(3-acrylamidophenylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)-3-methoxyphenylamino)azetidine-1-carboxylate

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   ConcentrationThe crude was concentrated under reduced pressure
2. 2
   Autrepurified

Mode opératoire

As shown in Scheme 2, a mixture of intermediate 1 of Scheme 2 (16 mg) and intermediate 1 of Scheme 1 (tert-butyl 3-(4-amino-3-methoxyphenylamino)azetidine-1-carboxylate, 20 mg) in dioxane (1.0 mL) with catalytic trifluoroacetic acid was stirred overnight at 50° C. The crude was concentrated under reduced pressure and purified using HPLC (TFA modifier) to give the title compound (10 mg) as a TFA salt. 1H-NMR (DMSO-d6, 400 MHz) δ 10.1 (s, 1H), 8.4 (br, 1H), 8.20 (s, 1H), 8.05 (s, 1H), 7.62 (br, 1H), 7.43 (br, 1H), 7.23-7.26 (m, 2H), 6.25 (dd, J=4, 10 Hz, 1H), 6.10-6.14 (m, 1H), 5.72 (d, J=10 Hz, 1H), 5.72 (d, J=10 Hz, 1H), 3.67-4.03 (m, 5H), 3.52-3.55 (m, 2H), 1.35 (s, 9H); calculated mass for C29H32F3N7O4: 599.3. found: 600.3 (M+H+).

Source