Cesium carbonate → 4-(2-(4-(Benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)cyclohex-3-enol

HRID 410236Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[S:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.F[C:25]1[C:30]([C:31]2[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH:32]=2)=[CH:29][CH:28]=[CH:27][N:26]=1.CN1C(=O)CCC1>C(OCC)(=O)C>[S:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:25]2[C:30]([C:31]3[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH:32]=3)=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 200 °C

Procedure

To a vial containing cesium carbonate (1391 mg, 4.27 mmol) was added 4-(benzo[d]thiazol-2-ylamino)phenol (1035 mg, 4.27 mmol), and 4-(2-fluoropyridin-3-yl)cyclohex-3-enol (330 mg, 1.708 mmol) followed by NMP (2.2 mL). The reaction was heated at 200° C. for 2 h with microwave irradiation. The black mixture was diluted with ethyl acetate and washed with 5N NaOH before drying over sodium sulfate, filtering, and concentrating under reduced pressure to a brown residue. Purification by column chromatography (ethyl acetate/dichlormethane) afforded 4-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)cyclohex-3-enol (44.8 mg, 0.108 mmol, 3, steps, 6.31% yield) as a pale brown oil. MS (ESI, pos. ion) m/z: 416.1 (M+1). IC50 (uM) +++++.

Workup

washwashed with 5N NaOH
dry with materialbefore drying over sodium sulfate
filtrationfiltering
concentrationconcentrating under reduced pressure to a brown residue
customPurification by column chromatography (ethyl acetate/dichlormethane)

Sources & evidence

ORD record: ord-434484a9482a461faac65da27af66f4e
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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