Water → HCID 59351141, compound

HRID 887429Notes

Reaction equation

F[C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[NH:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1.O>CN1C(=O)CCC1>[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[NH:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:2]2[C:3]([CH:8]3[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]3)=[N:4][CH:5]=[CH:6][N:7]=2)=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 125 °C

Procedure

Argon was bubbled through a mixture of (rac)3-(3-fluoropyrazin-2-yl)cyclohexanone (250 mg, 1.287 mmol), cesium carbonate (1258 mg, 3.86 mmol) and 4-(benzo[d]thiazol-2-ylamino)phenol (468 mg, 1.931 mmol) in NMP (3 ml) for 5 min. The mixture was heated to 125° C. for 3 hrs and was then cooled to RT. Distilled water (100 ml) was added and the resulting mixture was extracted with EtOAc (3×50 ml). The organic layer was washed with water and brine and dried over sodium sulfate. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (20% to 50% EtOAc in hexanes) afforded (rac)-3-(3-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyrazin-2-yl)cyclohexanone as a white solid. MS (ESI, pos. ion) m/z: 417.0 (M+1). IC50 (uM) +++++.

Workup

temperaturewas then cooled to RT
extractionthe resulting mixture was extracted with EtOAc (3×50 ml)
washThe organic layer was washed with water and brine
dry with materialdried over sodium sulfate
filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record: ord-385640e1b4714b5ca4a1ec90603cdc88
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247418B2

Reaction notes

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