Triethylamine → 1-(4-(thiazol-2-ylmethyl)-5,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one

HRID 2175741Notes

Reaction equation

Cl.[NH:2]1[CH2:7][CH:6]=[C:5]([CH2:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:21](Cl)(=[O:24])[CH:22]=[CH2:23]>C(Cl)Cl.O>[S:10]1[CH:11]=[CH:12][N:13]=[C:9]1[CH2:8][C:5]1[CH2:4][CH2:3][N:2]([C:21](=[O:24])[CH:22]=[CH2:23])[CH2:7][CH:6]=1

Participants

Conditions

Temperature: 27.5 °C

Procedure

To a stirred suspension of 2-((1,2,3,6-tetrahydropyridin-4-yl)methyl)thiazole hydrochloride (Intermediate-2) (1.57 g, 5.34 mmol) in anhydrous CH2Cl2 (20 mL) was added triethylamine (4.4 mL, 32.0 mmol), followed by acryloyl chloride (1.3 mL, 16.0 mmol) at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 16 h. Then the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get residue which was purified by column chromatography using a mixture of 20% ethyl acetate/hexane as an eluent to get the desired compound as a light brown liquid (320 mg, 26%); 1H NMR (400 MHz, DMSO-d6) δ 7.71 (d, J=3.4 Hz, 1H), 7.60 (d, J=2.9 Hz, 1H), 6.88-6.70 (m, 1H), 6.14-6.08 (m, 1H), 5.72-5.60 (m, 2H), 4.12-4.08 (m, 1H), 4.06-3.96 (m, 1H), 3.74-3.70 (m, 2H), 3.66-3.54 (m, 2H), 2.12-2.02 (m, 2H); ES-MS: 235.1 (M+1)+.

Workup

extractionextracted with ethyl acetate (2×50 mL)
washThe organic layer was washed with brine (50 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
customThe filtrate was rotary evaporated under vacuum
customto get residue which
customwas purified by column chromatography
additiona mixture of 20% ethyl acetate/hexane as an eluent

Sources & evidence

ORD record: ord-9344f28c2e8f4fa7b3f3f639bfa0b4d9
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062075B2

Reaction notes

Loading…