Potassium Hydroxide → HCID 68547061, compound

HRID 2241924Notes

Reaction equation

HRID 2241924 reaction equation
O.NN.[OH-].[K+].C(OC([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:34])[C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[OH:33])=[CH:20][C:19]=2[F:35])[CH2:13][CH2:12]1)=O)C.[Cl-].[NH4+]>C(O)CO.O>[Cl:32][C:30]1[CH:29]=[CH:28][C:27]([OH:33])=[C:26]([CH:31]=1)[C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)=[C:19]([F:35])[CH:20]=1)=[O:34]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 25517Ammonium ChlorideHCID 59204986HCID 59204986, compound

Product 1

HCID 68547061HCID 68547061, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

Hydrazine monohydrate (0.227 ml, 5.70 mmol) and potassium hydroxide (0.641 g, 11.4 mmol) were added to a solution of 4-{[4-(5-chloro-2-hydroxybenzoylamino)-2-fluorophenyl]amino}piperidine-1-carboxylic acid ethyl ester (compound of Reference Example 189; 0.500 g, 1.14 mmol) in ethyleneglycol (10 ml), and the mixture was refluxed for 1 hour. The reaction mixture was cooled to room temperature, and saturated aqueous ammonium chloride and water were added. The precipitated solid was collected by filtration and washed with water to give the title compound (0.267 g, 64%) as an ivory solid.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-85cea7c06ee4410daefd91cb12f3bef7
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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