Hydrazinecarboxaldehyde → HCID 57562696, compound

HRID 1725488Notes

Reaction equation

HRID 1725488 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-277635d6004e49b0b013349d27461346
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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