[CH3:1][N:2]([CH3:14])[C:3]([S:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)=[O:4].B.CSC.CO.[H][H]>C1COCC1>[CH3:1][N:2]([CH3:14])[C:3]([S:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1)=[O:4]Dissolve 4-dimethylcarbamoylthio-benzonitrile (3.07 g, 14.9 mmol) in anhydrous THF (30 mL). Add borane-dimethylsulfide complex (4.24 mL, 44.7 mmol, 1M solution in diethyl ether) and stir the mixture at room temperature for 3 h. Add methanol dropwise until hydrogen evolution ceases. Concentrate the mixture in vacuo and purify the crude mixture by SCX chromatography eluting with methanol and 2M ammonia in methanol to obtain the title compound as a slightly impure oil (2.9 g). Dissolve the oil (2.9 g) in DCM and add 2M hydrogen chloride in ether. Stir the mixture for 1 h and concentrate in vacuo to obtain a solid. Suspend the solid in DCM and add diethyl ether to precipitate the salt. Filter and dry the solid in vacuo to obtain the hydrochloride salt of the title compound as a white solid (2.33 g, 64%). Elute the compound through a SCX column to obtain the desired intermediate as an oil. MS (ES+) m/z: 211 (M+H)+.
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