Cesium carbonate → HCID 69940642, compound

HRID 714705Notes

Reaction equation

HRID 714705 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[Cl:15])[N:4]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]([CH2:29][C@H:30]([OH:35])[C:31]([F:34])([F:33])[F:32])[C:25](=[O:28])[NH:26][N:27]=2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]([CH2:29][C@H:30]([OH:35])[C:31]([F:33])([F:34])[F:32])[C:25](=[O:28])[N:26]([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[Cl:15])[N:4]=3)[N:27]=2)=[CH:19][CH:18]=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 67396148HCID 67396148, compound

Product 1

HCID 69940642HCID 69940642, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

259 mg (0.18 mmol) of the compound from Example 81A (purity about 20%) were dissolved in 2 ml of acetonitrile, and 62 mg (0.21 mmol) of the compound from Example 5A and 89 mg (0.27 mmol) of cesium carbonate were added. The mixture was stirred at 60° C. for 2.5 h and at RT for a further 96 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 31 mg of the target compound, which were subjected to a further chromatographic purification on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3, then 1:1). This gave 23 mg (22% 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]
  5. customThis gave 31 mg of the target compound, which were subjected to a further chromatographic purification on silica gel (mobile phase

Sources & evidence

ORD record
ord-c764165d649842eebd02194587b0883f
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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