Water → HCID 178513222, compound

HRID 1987943Notes

Reaction equation

HRID 1987943 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH2:7][C:8](=[C:13]1[C:26]3[CH:25]=[CH:24][C:23]([C:27]#[N:28])=[CH:22][C:21]=3O[C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[O:4].[NH2:31][OH:32].Cl.C([O-])([O-])=O.[K+].[K+].[OH2:40]>CCO>[OH:32][NH:31][C:27]([C:23]1[CH:22]=[CH:21][C:26]2[C:13](=[C:8]3[CH2:9][CH:10]4[N:5]([C:3](=[O:4])[C:2]([F:30])([F:29])[F:1])[CH:6]([CH2:12][CH2:11]4)[CH2:7]3)[C:14]3[C:15]([O:40][C:25]=2[CH:24]=1)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[NH:28]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 577253399-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carbonitrile

Product 1

HCID 178513222HCID 178513222, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of compound 5e (0.44 g, 1.07 mmol) in EtOH (5 mL) were added NH2OH.HCl (0.223 g, 3.19 mmol) and K2CO3 (0.3 g, 2.17 mmol). The reaction mixture was refluxed for 4 h. Upon cooling to room temperature, H2O (1 mL) was added to the mixture. The mixture was extracted with CH2Cl2 (2×5mL), dried (MgSO4), and concentrated to yield compound 6a. The product 6a was used in the next reaction without further purification. MS m/z (MH+) 443.9.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. extractionThe mixture was extracted with CH2Cl2 (2×5mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7efba73226a54ee79455cf77194303d5
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

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