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 335218Notes

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-f8d3840ab17f45ea82de9c4d6e491676
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883828B2

Reaction notes

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