Cesium carbonate → 3-(2-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyridin-3-YL)cyclopentanol

HRID 1880169Notes

Reaction equation

F[C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O.CCOC(C)=O>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:2]2[C:7]([CH:8]3[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A suspension of 3-(2-fluoropyridin-3-yl)cyclopentanol (869 mg, 4.80 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (2324 mg, 9.59 mmol) and cesium carbonate (3281 mg, 10.07 mmol) in N-methyl-2-pyrrolidinone (8 mL) was heated to 130° C. under nitrogen. After 9 h, the reaction was cooled to 23° C., diluted with EtOAc (500 mL) and washed with 1N NaOH solution (6×150 mL) and brine (150 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 1-4% methanol/dichloromethane), affording the product as a tan solid. MS (ESI, pos. ion) m/z: 404.1 (M+1). IC50 (uM) +++++.

Workup

temperaturethe reaction was cooled to 23° C.
washwashed with 1N NaOH solution (6×150 mL) and brine (150 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (eluant: 1-4% methanol/dichloromethane)

Sources & evidence

ORD record: ord-3bc981eba8f147079e1cf309b0a91044
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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