Diisopropylethylamine → HCID 86634785, compound

HRID 911074Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.Br[CH2:19][C:20](=O)[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>C(O)C>[Br:1][C:2]1[C:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:19]=[C:20]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:11]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A flask was charged with ethyl 2-(5-bromo-2-thioureidopyridin-4-yl)acetate (2.200 g, 6.914 mmol), 1-bromo-4-phenylbutan-2-one (1.884 g, 8.297 mmol), DIEA (1.806 mL, 10.37 mmol) and ethanol (100 mL). The mixture was heated stirred at 70° C. for 2 hours, then cooled. The reaction was concentrated, and the residue was partitioned between chloroform and dilute sodium bicarbonate solution. The organic phase was washed with dilute sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated. The solid residue was recrystallized from hexane/ethyl acetate to give the desired product (1.815 g, 58.81% yield) as a yellow solid.

Workup

temperatureThe mixture was heated
temperaturecooled
concentrationThe reaction was concentrated
customthe residue was partitioned between chloroform and dilute sodium bicarbonate solution
washThe organic phase was washed with dilute sodium bicarbonate solution
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe solid residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record: ord-7ffd0b2ca21e4f338cb256457443e8c4
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022222B2

Reaction notes

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