Triethylamine → {3-[5-(2-Methyl-benzoyl)-thiazol-2-ylamino]-propyl}-carbamic Acid tert-butyl Ester

HRID 2119587Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](=[O:7])[CH2:5]Br.[C:12]([O:16][C:17](=[O:30])[NH:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([N:25]=[CH:26]N(C)C)=[S:24])([CH3:15])([CH3:14])[CH3:13].CCN(CC)CC>C(O)C>[C:12]([O:16][C:17](=[O:30])[NH:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]1[S:24][C:5]([C:4](=[O:7])[C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=2[CH3:1])=[CH:26][N:25]=1)([CH3:13])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 613 mg (2.9 mmol) 2-methyl phenacylbromide (literature: WO9907666), 691 mg (2.4 mmol) [3-(3-Dimethylaminomethylene-thioureido)-propyl]-carbamic acid tert-butyl ester and 1 ml (7.2 mmol) NEt3 in 20 ml ethanol was heated to 100° C. for 16 h. The mixture was concentrated and purified by flash column chromatography on silica eluting with ethyl acetate/n-hexane 1/1. The combined product fractions were evaporated and 693 mg (77%) of the title compound (MS (m/e): 375.9 (MH+, 100%)) were obtained.

Workup

concentrationThe mixture was concentrated
custompurified by flash column chromatography on silica eluting with ethyl acetate/n-hexane 1/1
customThe combined product fractions were evaporated

Sources & evidence

ORD record: ord-ac2081fbf8ed4e0a9cafc485b7ea5b97
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686381B2

Reaction notes

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