Ethyl 2'-(acetylamino)-4'-methyl-4,5'-bi-1,3-thiazole-2-carboxylate → 2'-(Acetylamino)-N-allyl-4'-methyl-4,5'-bi-1,3-thiazole-2-carboxamide

HRID 1715261Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16]([O:18]CC)=O)[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]>C(N)C=C>[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16]([NH:9][CH2:8][CH:7]=[CH2:11])=[O:18])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

In a microwave tube, ethyl 2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazole-2-carboxylate, Compound (1), (1.0 g, 3.21 mmol, 1 eq.) is dissolved in allylamine (Fluka)(6 ml). The reaction mixture is heated at 80° C. for 20 min under microwave irradiation. The reaction is complete, but some desacetylation is observed. The solvents are evaporated and the crude product is recrystallized in MeOH. Compound (2) is isolated as pale yellow solid (492.9 mg; 47%). 1H NMR (DMSO-d6, 300 MHz) δ 2.15 (s, 3H), 2.50 (s, 3H), 3.91 (m, 2H), 5.10 (d, J=12 Hz, 1H), 5.17 (d, J=18 Hz, 1H), 5.88 (m, 1H), 7.99 (s, 1H), 8.94 (t, J=5 Hz, 1H), 12.14 (br s, 1H). M− (ESI): 321.17; M+ (ESI): 323.18. HPLC (method A), Rt: 2.84 min (purity: 99.6%).

Workup

customThe solvents are evaporated
customthe crude product is recrystallized in MeOH

Sources & evidence

ORD record: ord-fc1347c714324ebc990f2ce50e3e28ee
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799814B2

Reaction notes

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