Cesium carbonate → HCID 86690949, compound

HRID 714742Notes

Reaction equation

HRID 714742 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[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]([F:44])([F:43])[F:42])[C:32]([C:45]([O:47][CH3:48])=[O:46])=[CH:31][CH:30]=1>C(#N)C>[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[CH:34]=[C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:41]([F:42])([F:43])[F:44])[C:32]([C:45]([O:47][CH3:48])=[O:46])=[CH:31][CH:30]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 23436459HCID 23436459, compoundHCID 595368365-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 86690949HCID 86690949, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

179 mg (0.58 mmol) of the compound from Example 5A and 285 mg (0.88 mmol) of cesium carbonate were suspended in 5 ml of acetonitrile, and 340 mg (0.58 mmol) of the compound from Example 108A were added. The mixture was stirred under reflux for 4 h. The precipitated solid was then filtered off and the filtrate was concentrated under reduced pressure to a volume of about 1.5 ml. After addition of 0.5 ml of 1 N hydrochloric acid, the mixture was directly purified chromatographically [Method 19]. This gave 231 mg (65% of theory) of the target compound.

Workup

  1. temperatureunder reflux for 4 h
  2. filtrationThe precipitated solid was then filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure to a volume of about 1.5 ml
  4. additionAfter addition of 0.5 ml of 1 N hydrochloric acid
  5. customthe mixture was directly purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-30f9ad9afb254ba0b81fe94e9e0157b7
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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