1-Bromo-2-butanone → ethyl ((1S)-5-{3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 2235894Notes

Reaction equation

[NH2:1][C:2]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[C@H:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]3)=[C:6]([O:30][CH3:31])[CH:5]=1)=[S:3].Br[CH2:33][C:34](=O)[CH2:35][CH3:36]>CCO>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C@H:18]1[C:19]2[C:15](=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][C:7]3[CH:28]=[CH:29][C:4]([C:2]4[S:3][CH:33]=[C:34]([CH2:35][CH3:36])[N:1]=4)=[CH:5][C:6]=3[O:30][CH3:31])=[CH:21][CH:20]=2)[CH2:16][CH2:17]1)[CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

Ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (90 mg, 0.2 mmol) (Example 146) and 1-bromo-2-butanone (36.7 mg, 0.24 mmol) were dissolved in EtOH (anhydrous, 8 mL) and stirred at 70° C. for 6 h. The reaction was cooled to rt, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc:hexane (v/v)=1:2) gave 50 mg (51%) of the title compound as a clear oil. LC-MS: RT=4.07 min; (M+H)+ 496.2.

Workup

temperatureThe reaction was cooled to rt
concentrationconcentrated under reduced pressure
customPurification by silica gel flash chromatography (EtOAc:hexane (v/v)=1:2)

Sources & evidence

ORD record: ord-fd63903c7f4442d9bc61aeaa0c28c404
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714004B2

Reaction notes

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