Cesium carbonate → HCID 59326847, compound

HRID 410312Notes

Reaction equation

HRID 410312 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)=[O:17].F[C:26]1[C:31]([CH:32]2[CH2:36][CH2:35][C:34]([C:38]([F:41])([F:40])[F:39])([OH:37])[CH2:33]2)=[CH:30][CH:29]=[CH:28][N:27]=1.CN1C(=O)CCC1>C(OCC)(=O)C>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:26]2[C:31]([C@H:32]3[CH2:36][CH2:35][C@@:34]([OH:37])([C:38]([F:40])([F:41])[F:39])[CH2:33]3)=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:20][CH:19]=1)=[O:17]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanoneHCID 59326992HCID 59326992, compound

Product 1

HCID 59326847HCID 59326847, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
200 °C

Procedure

To a vial containing cesium carbonate (1634 mg, 5.02 mmol), (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (717 mg, 3.01 mmol), and 3-(2-fluoropyridin-3-yl)-1-(trifluoromethyl)cyclopentanol (500 mg, 2.006 mmol) was added NMP (13.400 ml). The mixture was heated at 200° C. for 5 h with microwave irradiation. The reaction mixture was diluted with ethyl acetate and washed with 5N NaOH before drying the organic layer over magnesium sulfate, filtering, and concentrating under reduced pressure. The resulting orange oil was purified by column chromatography (ethyl acetate/dichloromethane) to give a pale orange oil. The material was diluted with ethyl acetate and washed with water and 10 N NaOH before separating the mixture by SFC into its components, which consisted of two products identified as enantiomers by NMR. MS (ESI, pos. ion) m/z: 468.2 (M+1). IC50 (uM) +++++.

Workup

  1. washwashed with 5N NaOH
  2. dry with materialbefore drying the organic layer over magnesium sulfate
  3. filtrationfiltering
  4. concentrationconcentrating under reduced pressure
  5. customThe resulting orange oil was purified by column chromatography (ethyl acetate/dichloromethane)
  6. customto give a pale orange oil
  7. washwashed with water and 10 N NaOH
  8. custombefore separating the mixture by SFC into its components, which

Sources & evidence

ORD record
ord-d586d1c350434dc6afe2cdc798415f36
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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