Imidazole → {3-[(3-Imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester

HRID 1170480Notes

Reaction equation

[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:13]1[S:17][N:16]=[C:15](Cl)[N:14]=1)[CH3:12])([CH3:4])([CH3:3])[CH3:2].[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.[H-].[Na+]>CS(C)=O.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:13]1[S:17][N:16]=[C:15]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)[N:14]=1)[CH3:12])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

{3-[(3-Chloro-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester (6.50 g, 21.2 mmol) was combined with imidazole (7.20 g, 105 mmol) and dissolved in DMSO (100 mL). Next, the sodium hydride (833 mg of a 60% dispersion on mineral oil, 57.8 mmol) was added the reaction mixture was stirred at 60° C. overnight. After this period, brine was added to the reaction mixture and it was transferred to a separatory funnel. The product was extracted with copious DCM and the organic layer was dried over anhydrous Na2SO4. The crude material was purified by flash silica chromatography (Hex to 1:4 Hex/EtOAc) to yield 6.78 g (94%) of {3-[(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester as a clear oil. [M+H]+ 339.10.

Workup

waitAfter this period
customwas transferred to a separatory funnel
extractionThe product was extracted with copious DCM
dry with materialthe organic layer was dried over anhydrous Na2SO4
customThe crude material was purified by flash silica chromatography (Hex to 1:4 Hex/EtOAc)

Sources & evidence

ORD record: ord-e6758f21792f494b9ab4e7ff01aa9dff
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825256B2

Reaction notes

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