Triethylamine → ethyl 3-(5-bromo-2-(4-phenethylthiazol-2-ylamino)-Pyridin-4-yloxy)-4-chlorobenzoate

HRID 911038Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=2[Cl:24])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.Br[CH2:26][C:27](=O)[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=2[Cl:24])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:26]=[C:27]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:11]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A flask was charged with ethyl 3-(5-bromo-2-thioureidopyridin-4-yloxy)-4-chlorobenzoate (0.200 g, 0.464 mmol), 1-bromo-4-phenylbutan-2-one (0.105 g, 0.464 mmol) and triethylamine (0.0470 g, 0.464 mmol). Ethanol (5 mL) was added and the reaction was heated at 70° C. for 6 hours, and then concentrated to provide ethyl the desired product (0.250 g, 95 yield) as white solid. LC/MS (apci) M+2H: 560 (100%).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-1d01b8808b54441bbb5743dd3cf3c68f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022222B2

Reaction notes

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