4-Butylbenzoyl chloride → HCID 54468846, compound

HRID 1735906Notes

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]2

Participants

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, I 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 (3x) 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 (3x)
dry with materialthe combined extracts were dried (MgSO4)
concentrationconcentrated
customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-45134d4a1c7841ec8f09ae316e66b4d8
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05538988

Reaction notes

Loading…