1-(5-Bromo-3-phenoxypyridin-2-yl)thiourea → Methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)-2-methoxy-2-methylpropanoate

HRID 911896Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.Br[CH2:20][C:21](=O)[CH2:22][C:23]([O:29][CH3:30])([CH3:28])[C:24]([O:26][CH3:27])=[O:25]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:5]([NH:8][C:9]2[S:10][CH:20]=[C:21]([CH2:22][C:23]([O:29][CH3:30])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])[N:11]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

In a 125 mL round-bottom flask, 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (0.50 g, 1.54 mmol) (prepared as described in Example 10, Steps A-D) and methyl 5-bromo-2-methoxy-2-methyl-4-oxopentanoate (0.586 g, 2.31 mmol) were dissolved in dry THF (25 mL), heated to 50° C. and agitated overnight. The solvent was evaporated and the residue was dissolved in chloroform and washed with diluted sodium bicarbonate solution twice, dried over magnesium sulfate, filtered and evaporated. The resulting solid was purified by chromatography on silica gel, eluted with 10-15% ethyl acetate/hexane to give the title compound (0.485 g, 65.7% yield) as yellow solid. 1H NMR (CDCl3) δ 1.46 (s, 3H), 3.12 (s, 2H), 3.34 (s, 3H), 3.73 (s, 3H), 6.58 (s, 1H), 7.06-7.45 (m, 6H), 8.11 (s, 1H), 8.64 (bs, 1H).

Workup

customThe solvent was evaporated
dissolutionthe residue was dissolved in chloroform
washwashed with diluted sodium bicarbonate solution twice
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe resulting solid was purified by chromatography on silica gel
washeluted with 10-15% ethyl acetate/hexane

Sources & evidence

ORD record: ord-5cd95f08d45f42819658b8be3a34d50f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022223B2

Reaction notes

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