Triethylamine → Ethyl 1-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}cyclopropane carboxylate

HRID 1436377Notes

Reaction equation

C(N(CC)CC)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][S:17][C:18]#[N:19])=[CH:11][CH:10]=1.[Cl-].[CH2:22]([O:24][C:25]([C:27]1([NH3+:30])[CH2:29][CH2:28]1)=[O:26])[CH3:23]>C(O)C>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[C:18]([NH:30][C:27]3([C:25]([O:24][CH2:22][CH3:23])=[O:26])[CH2:29][CH2:28]3)[S:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Triethylamine (3.1 mL, 22.3 mmol) was added under nitrogen to a mixture of 2-(4-bromophenyl)-2-oxoethyl thiocyanate (5.2024 g, 20.3 mmol), prepared in step 1 of Example 1, and 1-ethoxycarbonyl-cyclopropyl-ammonium chloride (3.7001 g, 22.3 mmol), prepared in the previous step, in 400 mL of absolute ethanol. After the addition, the reaction was stirred at 65° C. for 4 days. The reaction was concentrated under reduced pressure to remove the ethanol. The residue was taken up in methylene chloride, applied to a Biotage FLASH 25+™ cartridge and the methylene chloride allowed to evaporate. Purification of the residue on the samplet on a Horizon™ Flash Collector (the Biotage FLASH 25+™ cartridge) using a linear gradient of 5% ethyl acetate-hexane to 100% ethyl acetate gave ethyl 1-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}cyclopropane carboxylate (2.66 g, 36%) as a light yellow solid, mp 152-154° C.; MS m/z 367.

Workup

additionAfter the addition
concentrationThe reaction was concentrated under reduced pressure
customto remove the ethanol
customto evaporate
customPurification of the residue on the samplet on a Horizon™ Flash Collector (the Biotage FLASH 25+™ cartridge)

Sources & evidence

ORD record: ord-906ab058c90e44d79ffa5e3b81577ad4
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618990B2

Reaction notes

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