Ethyl formimidate hydrochloride → N-[4-(2-{4-[(iminomethyl)amino]phenyl)ethyl)-1,3-thiazol-2-yl]acetamide

HRID 2117922Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1.Cl.[CH:20](=[NH:24])OCC>C1COCC1>[NH:24]=[CH:20][NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-{4-[2-(4-Aminophenyl)ethyl]-1,3-thiazol-2-yl}acetamide (150 mg) was dissolved in THF (2 ml) and pH=7 buffer (2 ml). Then, ethyl imidoformate hydrochloride (1.26 g) was added to the solution at 0° C. The reaction mixture was stirred at 0° C. for 2 hours, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with CH3CN/water (7:3) as an eluent. The oil was purified again by preparative silica gel chromatography with CHCl3/MeOH (5:1) as an eluent to give N-[4-(2-{4-[(iminomethyl)amino]phenyl}ethyl)-1,3-thiazol-2-yl]acetamide (110 mg) as pale brown oil.

Workup

concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography over silica gel with CH3CN/water (7:3) as an eluent
customThe oil was purified again by preparative silica gel chromatography with CHCl3/MeOH (5:1) as an eluent

Sources & evidence

ORD record: ord-fef4f359494343d49ad00ea1df4b50a4
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442715B2

Reaction notes

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