Triethylamine → {3-[4-(2-Methyl-benzoyl)-thiazol-2-ylamino]-propyl}-carbamic Acid tert-butyl Ester

HRID 2119596Notes

Reaction equation

Br[CH2:2][C:3](=O)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=[O:5].[C:14]([O:18][C:19](=[O:28])[NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([NH2:27])=[S:26])([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC>CO>[C:14]([O:18][C:19](=[O:28])[NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]1[S:26][CH:2]=[C:3]([C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:12])[N:27]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2.55 g (10.6 mmol) 3-Bromo-1-o-tolyl-propane-1,2-dione, 1.9 g (8.1 mmol) (3-thioureido-propyl)-carbamic acid tert-butyl ester and 5.66 ml (40.6 mmol) NEt3 in 100 ml methanol was heated to 80° C. for 2 h. The reaction mixture was evaporated under reduced pressure and the residue was purifier by flash column chromatography on silica eluting with a gradient of heptane and ethyl acetate. Evaporation of the product fractions yielded 2.17 g (71%) of the title compound as dark red oil.

Workup

customThe reaction mixture was evaporated under reduced pressure
customEvaporation of the product fractions

Sources & evidence

ORD record: ord-1eacff90af794625ae8ec969a65eaac2
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686381B2

Reaction notes

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