Cesium carbonate → HCID 86690928, compound

HRID 714703Notes

Reaction equation

HRID 714703 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]=[C:11]([Cl:15])[C:10]=2[Cl:16])[CH:4]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]([CH2:30][C@H:31]([OH:36])[C:32]([F:35])([F:34])[F:33])[C:26](=[O:29])[NH:27][N:28]=2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]([CH2:30][C@H:31]([OH:36])[C:32]([F:34])([F:35])[F:33])[C:26](=[O:29])[N:27]([CH2:2][C:3]3[CH:8]=[CH:7][N:6]=[C:5]([C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=4[Cl:16])[CH:4]=3)[N:28]=2)=[CH:20][CH:19]=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 67398997HCID 67398997, compound

Product 1

HCID 86690928HCID 86690928, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

81 mg (0.26 mmol) of the compound from Example 66A were dissolved in 3 ml of acetonitrile and 79 mg (0.26 mmol) of the compound from Example 5A and 125 mg (0.38 mmol) of cesium carbonate were added. The mixture was stirred at 65° C. for 2 h and at RT for a further 16 h. The solid was then filtered off and rinsed with a little acetonitrile. The filtrate was concentrated under reduced pressure and directly purified chromatographically [Method 19]. This gave 79 mg (56% of theory) of the target compound.

Workup

  1. filtrationThe solid was then filtered off
  2. washrinsed with a little acetonitrile
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customdirectly purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-da7df0f259ce43cb92018588223c0b15
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

Loading…