Cesium carbonate → HCID 86690927, compound

HRID 714701Notes

Reaction equation

HRID 714701 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])[CH:4]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:27]([CH2:32][C@H:33]([OH:38])[C:34]([F:37])([F:36])[F:35])[C:28](=[O:31])[NH:29][N:30]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:27]([CH2:32][C@H:33]([OH:38])[C:34]([F:36])([F:37])[F:35])[C:28](=[O:31])[N:29]([CH2:2][C:3]3[CH:8]=[CH:7][N:6]=[C:5]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:15]([F:18])([F:17])[F:16])[CH:4]=3)[N:30]=2)=[CH:22][CH:21]=1

Participants

5

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 67395877HCID 67395877, compound

Product 1

HCID 86690927HCID 86690927, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

145 mg (0.46 mmol) of the compound from Example 64A were dissolved in 3 ml of acetonitrile, and 141 mg (0.46 mmol) of the compound from Example 5A and 224 mg (0.69 mmol) of cesium carbonate were added. The mixture was stirred at 60° C. for 16 h. After cooling to RT, the solid was filtered off and rinsed with a little acetonitrile. Under reduced pressure, the filtrate was reduced to a volume of about 2 ml, 0.1 ml of 1 N hydrochloric acid was added and the product was directly purified chromatographically [Method 19]. This gave 49 mg (20% of theory) of the target compound.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe solid was filtered off
  3. washrinsed with a little acetonitrile
  4. additionwas added
  5. customthe product was directly purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-3d3892c6d06847b09a1b6b71c89a8abb
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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