Hydrazinecarboxaldehyde → HCID 57562696, compound

HRID 1172432Notes

Reaction equation

HRID 1172432 reaction equation
[Cl:1][C:2]1[C:3]([F:31])=[C:4]([CH:28]=[CH:29][CH:30]=1)[C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)[N:21]=2)[C:17]#[N:18])[CH2:9][CH2:8]1)=[O:6].C[O-].[Na+].CO.[CH:37]([NH:39][NH2:40])=O>CO>[Cl:1][C:2]1[C:3]([F:31])=[C:4]([CH:28]=[CH:29][CH:30]=1)[C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[N:21]=[C:20]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)[CH:19]=[C:16]([C:17]3[NH:40][N:39]=[CH:37][N:18]=3)[CH:15]=2)[CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 12229Hydrazinecarboxaldehyde2×HCID 23694274Sodium methanolate methanolHCID 57562608HCID 57562608, compound

Product 1

HCID 57562696HCID 57562696, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a mixture of 25.2 mg of 2-((4-(3-chloro-2-fluorobenzoyl)piperazin-1-yl)methyl)-6-(thiazol-2-ylamino)isonicotinonitrile obtained in Example 104 and 1 ml of methanol was added 0.3 ml of a 28% sodium methoxide-methanol solution, followed by stirring at room temperature for 5 hours. To the reaction solution was added a solution of 3.3 mg of formohydrazide in 1 ml of methanol. The reaction mixture was stirred at room temperature for 17 hours, and then heated under reflux for 24 hours. To the reaction solution was added a solution of 16.6 mg of formohydrazide in 1.5 ml of methanol, and further heated under reflux for 22 hours. The reaction solution was cooled to room temperature, and then concentrated. The resulting residue was purified by a thin-layer chromatography for fractionation (eluent: chloroform/methanol=7/1) to give the title compound.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 17 hours
  2. temperatureheated
  3. temperatureunder reflux for 24 hours
  4. temperaturefurther heated
  5. temperatureunder reflux for 22 hours
  6. temperatureThe reaction solution was cooled to room temperature
  7. concentrationconcentrated
  8. customThe resulting residue was purified by a thin-layer chromatography for fractionation (eluent: chloroform/methanol=7/1)

Sources & evidence

ORD record
ord-269dc66b92bf424aa894b32687f5ed18
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

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