Hydrazine → HCID 58215751, compound

HRID 593640Notes

Reaction equation

HRID 593640 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:30]#[N:31])=[C:7]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH2:18][N:19]4C(=O)C5C(=CC=CC=5)C4=O)[CH:17]=3)[N:8]2[CH3:11])=[CH:4][CH:3]=1.NN>C(O)C>[NH2:19][CH2:18][C:16]1[CH:17]=[C:12]([C:7]2[N:8]([CH3:11])[C:9]3[C:5]([C:6]=2[C:30]#[N:31])=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=3)[CH:13]=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58215830HCID 58215830, compound

Product 1

HCID 58215751HCID 58215751, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-chloro-2-[5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-pyridin-3-yl]-1-methyl-1H-indole-3-carbonitrile (8.96 g, 18.89 mmol) in ethanol (200 mL) is added hydrazine (12.10 mL, 378 mmol) and the reaction mixture is stirred overnight. The mixture is then filtered and the solids are washed with ethyl acetate. The filtrate is partially concentrated to remove ethyl acetate. 1M aqueous HCl is added, and the aqueous mixture is washed with EtOAc. The aqueous layer is then basified with 4M aqueous NaOH and extracted with dichloromethane thrice. The dichloromethane extracts are dried over Na2SO4 and concentrated in vacuo to afford 2-(5-aminomethyl-pyridin-3-yl)-6-chloro-1-methyl-1H-indole-3-carbonitrile as a solid. MS (ESI) m/z 297.0 (M+H)+

Workup

  1. filtrationThe mixture is then filtered
  2. washthe solids are washed with ethyl acetate
  3. concentrationThe filtrate is partially concentrated
  4. customto remove ethyl acetate
  5. addition1M aqueous HCl is added
  6. washthe aqueous mixture is washed with EtOAc
  7. extractionextracted with dichloromethane thrice
  8. dry with materialThe dichloromethane extracts are dried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5684cf34aa94f3398e5f0d87ed3396f
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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