1,3,4-Thiadiazol-2-amine → 3-cyclopentyl-2-phenyl-N-[1,3,4]thiadiazol-2-yl-propionamide
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.CCN(C(C)C)C(C)C.[CH:16]1([CH2:21][CH:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](Cl)=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl>[CH:16]1([CH2:21][CH:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:23]([NH:1][C:2]2[S:3][CH:4]=[N:5][N:6]=2)=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17]1Participants
Procedure
To 2-amino-1,3,4-thiadiazole (220 mg, 21 mmol), 0.4 mL DIEA and 7 mL of DCM is added a solution of the title C compound, 3-cyclopentyl-2-phenylpropionyl chloride (500 mg, 21 mmol) in 2 mL of DCM. The mixture is stirred at ambient temperature for 2-3 h, the mixture is evaporated, and the residue is treated with 10 mL 1 N HCl and extracted twice with ethyl acetate. The combined extracts are washed with brine, saturated sodium bicarbonate solution, and brine and dried over anhydrous magnesium sulfate. Filtration and evaporation afford 3-cyclopentyl-2-phenyl-N-[1,3,4]thiadiazol-2-yl-propionamide as an orange foam: 1H NMR (400 MHz, DMSO-d6) δ 11 (m, 2H), 1.4 (m, 2H), 1.5 (m, 3H), 1.7(m, 3H), 2.1 (ddd, J=13.3, 7.8, 7.7 Hz, 1H), 4.0 (dd, J=8.1, 7.1 Hz, 1H), 7.2 (s, 1H), 7.3 (m, 4H), 9.1 (s, 1H), 12.8 (s, 1H); LC/MS 302 (M+1), 300 (M−1).
Workup
- customthe mixture is evaporated
- additionthe residue is treated with 10 mL 1 N HCl
- extractionextracted twice with ethyl acetate
- washThe combined extracts are washed with brine, saturated sodium bicarbonate solution, and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationFiltration and evaporation
Sources & evidence
- ORD record
- ord-5a023da167324707bf97795662a8f69a
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08252931B2
Reaction notes
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