Water → HCID 178456700, compound

HRID 433011

Reaction equation

Br[CH:2]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]=[N:10][N:11]([CH:12]([CH3:14])[CH3:13])[C:7]=2[CH:6]=1)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[C:31]([C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)(=[NH:33])[NH2:32].O>CN(C)C=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:2]2[N:33]=[C:31]([C:34]3[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=3)[NH:32][C:3]=2[C:5]2[CH:16]=[CH:15][C:8]3[N:9]=[N:10][N:11]([CH:12]([CH3:14])[CH3:13])[C:7]=3[CH:6]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 29 mg of 2-bromo-2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone in 0.38 mL of N,N-dimethylformamide was added 75 mg of cesium carbonate and 24 mg of 3-amidinopyridine hydrochloride. The mixture was heated at 50° C. for 30 min. The orange-brown mixture was cooled to 22° C., transferred to a separatory funnel with water, and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried (sodium sulfate), filtered, and the filtrate was concentrated to an orange oil. This oil was purified by flash chromatography (eluting with ethyl acetate) to give 12 mg of 6-[5-(4-fluoro-phenyl)-2-pyridin-3-yl-3H-imidazol-4-yl]-1-isopropyl-1H-benzotriazole as a white solid. LCMS m/z 399 (M+1).

Workup

temperatureThe orange-brown mixture was cooled to 22° C.
extractionextracted with ethyl acetate (3×)
washThe combined organic layers were washed with brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationthe filtrate was concentrated to an orange oil
customThis oil was purified by flash chromatography (eluting with ethyl acetate)

Sources & evidence

ORD record: ord-cd4a29b579b448c4a6427bdd90aad16a
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664395B2

Linked notes

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