3-butyl-5-tert-butyl-1,3-thiazol-2(3H)-imine hydroiodide → HCID 178448481, compound

HRID 254648Notes

Reaction equation

I.[CH2:2]([N:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[S:8][C:7]1=[NH:15])[CH2:3][CH2:4][CH3:5].[C:16]1([N:26]=[C:27](OCC)[CH2:28][CH3:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>C(O)CCC>[CH2:2]([N:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[S:8]/[C:7]/1=[N:15]\[C:27](=[N:26][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[CH2:28][CH3:29])[CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 85 °C

Procedure

To a 20-ml scintillation vial containing a magnetic stir bar were added the free base of Example 6A and the liquid imidate from Example 73A. Butanol was added to form a yellow solution. The reaction was heated to 85° C. in a heated shaker block and stirred for 48 h. The volatiles were removed by rotary evaporator to give a brown oil. Product purified by flash chromatography (silica gel: 5-40% ethyl acetate in hexanes) to give the title compound as a colorless oil. 1H NMR (DMSO-d6) δ0.96 (t, J=7.3 Hz, 3H), 1.04 (t, J=7.5 Hz, 3H), 1.24 (s, 9H) 1.29-1.42 (m, 2H), 1.73-1.83 (m, 2H), 2.18 (q, J=7.5 Hz, 2H), 4.13 (t, J=7.1 Hz, 2H), 6.76 (dd, J=7.3, 1.2 Hz, 1H), 7.13 (s, 1H), 7.38-7.55 (m, 4H), 7.83-7.88 (m, 2H). MS (ESI+) m/z 394 (M+H)+.

Workup

additionTo a 20-ml scintillation vial containing a magnetic stir bar
customto form a yellow solution
customThe volatiles were removed by rotary evaporator
customto give a brown oil
customProduct purified by flash chromatography (silica gel: 5-40% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-fc22ed4219b84a9db2fc194a932d57ee
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875640B2

Reaction notes

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