Cesium carbonate → HCID 46215027, compound

HRID 410314Notes

Reaction equation

F[C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][C:10]([CH3:14])([OH:13])[CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:2]2[C:7]([C@H:8]3[CH2:12][CH2:11][C@:10]([OH:13])([CH3:14])[CH2:9]3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:28][CH:27]=1)=[O:25]

Participants

Conditions

Temperature: 180 °C

Procedure

To a vial containing 3-(2-fluoropyridin-3-yl)-1-methylcyclopentanol (570 mg, 2.92 mmol), (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (1043 mg, 4.38 mmol), and cesium carbonate (2378 mg, 7.30 mmol) was added NMP (5.389 mL) before sealing and purging the vessel of air with nitrogen. The reaction mixture was set to heated at 180° C. for 5 h with microwave irradiation. It was diluted with ethyl acetate and washed with 5 N NaOH. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to a brown oil. The crude mixture of diastereomers was purified by SFC to yield four compounds. MS (ESI, pos. ion) m/z: 414.2 (M+1). IC50 (uM) +++++.

Workup

custompurging the vessel of air with nitrogen
additionIt was diluted with ethyl acetate
washwashed with 5 N NaOH
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure to a brown oil
additionThe crude mixture of diastereomers
customwas purified by SFC
customto yield four compounds

Sources & evidence

ORD record: ord-0a961c5ece494bc391de0f6cce013bf9
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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