1-Bromo-4-methyl-2-pentanone → 1-(5-Bromo-4-(4-isobutylthiazol-2-yl)pyridin-2-yl)-3-ethylurea

HRID 1047164Notes

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](=O)[CH2:20][CH:21]([CH3:23])[CH3:22]>CCO>[Br:1][C:2]1[C:3]([C:14]2[S:16][CH:18]=[C:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[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 100 mL round-bottomed flask 5-bromo-2-(3-ethylureido)pyridine-4-carbothioamide (Intermediate 6, 0.95 g, 3.13 mmol) and 1-bromo-4-methylpentan-2-one (0.561 g, 3.13 mmol, Chem. Pharm. Bull., 2001, 49(8), 988-998) were mixed in EtOH (10 mL) to give a yellow suspension. The reaction mixture was heated to 80° C. for 3 h. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. ACN was added, and the residue solid was azeotroped with ACN (3×). The crude mass obtained, 1.02 g, was taken forward without purification.

Workup

customto give a yellow suspension
temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
additionACN was added
customthe residue solid was azeotroped with ACN (3×)
customThe crude mass obtained
custom1.02 g, was taken forward without purification

Sources & evidence

ORD record: ord-2c3255f3b5ca4a8596774fe1b127d52d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569484B2

Reaction notes

Loading…