4-Butylbenzoyl chloride → HCID 54468846, compound
Reaction equation
[NH2:1][CH2:2][C:3]1[N:7]([C@H:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([F:19])=[CH:13][C:14]=3[F:18])[CH2:9]2)[C:6](=[S:20])[NH:5][CH:4]=1.[CH2:21]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)[CH2:22][CH2:23][CH3:24]>N1C=CC=CC=1>[F:18][C:14]1[CH:13]=[C:12]([F:19])[CH:11]=[C:10]2[C:15]=1[CH2:16][CH2:17][C@H:8]([N:7]1[C:3]([CH2:2][NH:1][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][C:25]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:26][CH:27]=3)=[CH:4][NH:5][C:6]1=[S:20])[CH2:9]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of (S)-5-aminomethyl-1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (0.30 g, 1 mmol), prepared as in Example 31, and 4-butylbenzoyl chloride (0.21 mL, 1.1 mmol) in 10 mL of dry pyridine was stirred under argon at approximately 0° C. for 1 hour and then at approximately 25° C. for an additional 2 hours. The mixture was concentrated and the residue was treated with water. The mixture was extracted with ethyl acetate (3×) and the combined extracts were dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate to give (S)-N-[3-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl]-4-butylbenzamide (0.25 g, 0.55 mmol), m.p. 242°-243° C.
Workup
- waitat approximately 25° C. for an additional 2 hours
- concentrationThe mixture was concentrated
- additionthe residue was treated with water
- extractionThe mixture was extracted with ethyl acetate (3×)
- dry with materialthe combined extracts were dried (MgSO4)
- concentrationconcentrated
- customThe residue was recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-1dd882c2a04740508f4d65ffe1e98e96
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719280
Reaction notes
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