Hydrazine → HCID 24993750, compound

HRID 1961019Notes

Reaction equation

HRID 1961019 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:39])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([NH:14][C@@H:15]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([F:38])([F:37])[F:36])[CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)=[O:13])[S:10][CH:11]=1.NN>C1COCC1.CO>[NH2:17][CH2:16][C@@H:15]([NH:14][C:12]([C:9]1[S:10][CH:11]=[C:7]([C:6]2[N:5]([CH3:39])[N:4]=[CH:3][C:2]=2[Cl:1])[CH:8]=1)=[O:13])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]([F:38])([F:37])[F:36]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57826490HCID 57826490, compound

Product 1

HCID 24993750HCID 24993750, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-2-thiophenecarboxamide (150 mg, 0.262 mmol) in THF-MeOH (1:1, 2 mL) was added hydrazine (123 uL, 2.62 mmol). After 12 h, the solution was filtered and the filtrate was concentrated, dry loaded onto silica and purified via column chromatography (2% MeOH in DCM (1% NH4OH)) affording the free base of the title compound.

Workup

  1. filtrationthe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customdry loaded onto silica
  4. custompurified via column chromatography (2% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-cbafb7fc180e425abfdc9e50731b87ce
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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