Water → HCID 53378621, compound

HRID 714673Notes

Reaction equation

HRID 714673 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([O:24]C)=O)[N:9]=2)=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33]/[C:34](=[N:36]/O)/[NH2:35].C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][C:34]1[N:35]=[C:22]([CH2:21][N:10]2[C:11](=[O:20])[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:16])([F:18])[F:17])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:9]2)[O:24][N:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24688406HCID 24688406, compoundHCID 59536841HCID 59536841, compound

Product 1

HCID 53378621HCID 53378621, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 mg (0.13 mmol) of the compound from Example 7A were dissolved in 2 ml of toluene, 51 mg (0.28 mmol) of (1Z)-2-(2-chlorophenyl)-N′-hydroxyethaneimidamide and 38 mg (0.28 mmol) of potassium carbonate were added and the mixture was heated under reflux for 6 h. For work-up, 10 ml of water were added and the mixture was extracted twice with in each case 10 ml of ethyl acetate. The combined organic phases were washed once with 10 ml of water and 10 ml of saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 40 mg (59% of theory) of the target compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 h
  3. extractionthe mixture was extracted twice with in each case 10 ml of ethyl acetate
  4. washThe combined organic phases were washed once with 10 ml of water and 10 ml of saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-92becaaf3ac846b6a88647011357f432
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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