Cesium carbonate → HCID 69940235, compound

HRID 714676Notes

Reaction equation

HRID 714676 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][C@H:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]1[S:30][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])=[N:32][N:33]=1>C(#N)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][C@H:15]([OH:20])[C:16]([F:18])([F:19])[F:17])[C:10](=[O:13])[N:11]([CH2:28][C:29]3[S:30][C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[Cl:40])=[N:32][N:33]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 595368365-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneHCID 67409044HCID 67409044, compound

Product 1

HCID 69940235HCID 69940235, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

30 mg (0.10 mmol) of the compound from Example 5A were dissolved in 3 ml of acetonitrile, and 48 mg (0.15 mmol) of cesium carbonate and 28 mg (0.10 mmol) of the compound from Example 86A were added. The mixture was stirred at 70° C. for 8 h. For work-up, the mixture was cooled to RT, diluted with 5 ml of methanol and filtered. The filtrate was concentrated under reduced pressure and the crude product was then purified chromatographically [Method 19]. This gave 11 mg (22% of theory) of the target compound.

Workup

  1. temperatureFor work-up, the mixture was cooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe crude product was then purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-cb30517ae80447d3a93578fc686efe8e
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

Loading…