Trifluoroacetic acid → 3-mercapto-N-methyl-N-(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)propanamide

HRID 1911974Notes

Reaction equation

C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH3:15][N:16]([C:41]1[S:42][C:43]([C:46]2[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=2)=[N:44][N:45]=1)[C:17](=[O:40])[CH2:18][CH2:19][S:20]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl.C(=O)(O)[O-].[Na+]>[SH:20][CH2:19][CH2:18][C:17]([N:16]([CH3:15])[C:41]1[S:42][C:43]([C:46]2[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=2)=[N:44][N:45]=1)=[O:40]

Participants

Conditions

Temperature: 23 °C

Procedure

Triethylsilane (76 μL, 0.48 mmol, 5.0 equiv) and trifluoroacetic acid (710 μL, 5.7 mmol, 100 equiv) were sequentially added to a stirred solution of N-methyl-N-(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)-3-(tritylthio)propanamide (50 mg, 0.096 mmol, 1.0 equiv) in dichloromethane (1.3 mL) at 23° C. The resulting solution was stirred at 23° C. for 30 m. The reaction mixture was diluted with a saturated solution of sodium bicarbonate (40 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried (Na2SO4), gravity-filtered, and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (ethyl acetate) to afford the title compound as a white powder (23 mg, 85%): mp 149-151° C.; 1H NMR (300 MHz, CDCl3) δ 9.17 (br s, 1H), 8.71 (m, 1H), 8.29 (m, 1H), 7.44 (dd, J=8, 5 Hz, 1H), 3.87 (s, 3H), 2.91-310 (m, 4H), 1.87 (t, J=8 Hz, 1H); ESIMS m/z 281 ([M+H]+).

Workup

extractionextracted with ethyl acetate (3×30 mL)
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationgravity-filtered
concentrationconcentrated by rotary evaporation
customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-1b381b5a9d9b44d5a63b59c86ed334ee
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604211B2

Reaction notes

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