Triethylamine → ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate

HRID 444697Notes

Reaction equation

Cl[C:2]([C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1)=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[Cl:19][C:20]1[C:21]([CH2:30][CH2:31][NH2:32])=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1.C(N(CC)CC)C>O1CCCC1>[Cl:17][C:12]1[C:11](/[C:2](/[NH:32][CH2:31][CH2:30][C:21]2[C:20]([Cl:19])=[CH:25][C:24]([C:26]([F:29])([F:28])[F:27])=[CH:23][N:22]=2)=[C:3](\[C:9]#[N:10])/[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.1 g, 0.369 mmol, 1 eq.) in 5 ml of tetrahydrofuran were added 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine hydrochloride (0.106 g, 0.40 mmol, 1.1 eq.) and triethylamine (TEA) (0.112 g, 1.10 mmol, 3 eq.) at room temperature. After being stirred for 8 h at 80° C., the mixture was evaporated. The residue was diluted with AcOEt and the precipitate was filtered off. The filtrate was evaporated and the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate (0.170 g, 99% yield).

Workup

customthe mixture was evaporated
additionThe residue was diluted with AcOEt
filtrationthe precipitate was filtered off
customThe filtrate was evaporated

Sources & evidence

ORD record: ord-4e641171f47a466598a9bbece19d4268
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476197B2

Reaction notes

Loading…