2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-one → 1-(5-bromo-4-(4-(1-methyl-1H-pyrazol-4-yl)thiazol-2-yl)pyridin-2-yl)-3-ethylurea

HRID 1047177Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:14](=[S:16])[NH2:15])=[CH:4][C:5]([NH:8][C:9]([NH:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1.Br[CH2:18][C:19]([C:21]1[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=1)=O>C(O)C>[Br:1][C:2]1[C:3]([C:14]2[S:16][CH:18]=[C:19]([C:21]3[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=3)[N:15]=2)=[CH:4][C:5]([NH:8][C:9]([NH:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 25 mL flask 5-bromo-2-(3-ethylureido)pyridine-4-carbothioamide (Intermediate 6, 478 mg, 1.58 mmol) and 2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethanone (Intermediate 96, 352 mg, 1.73 mmol) were suspended in ethanol (10 mL). The reaction mixture was heated at 80° C. for 12 h, cooled to room temperature and concentrated to one half the volume under reduced pressure. The resulting solids were filtered and washed with acetonitrile. Isolation gave 640 mg of the title compound as an off-white solid.

Workup

temperaturecooled to room temperature
concentrationconcentrated to one half the volume under reduced pressure
filtrationThe resulting solids were filtered
washwashed with acetonitrile

Sources & evidence

ORD record: ord-4f527f43000748e0819e790b5e126b20
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569484B2

Reaction notes

Loading…