Acetic Acid → HCID 86637186, compound

HRID 1854483Notes

Reaction equation

HRID 1854483 reaction equation
[Cl:1][C:2]1[C:3]([C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=O)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[NH2:19][NH2:20].CC(O)=O>CCO>[Cl:1][C:2]1[C:3]([C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:19][NH2:20])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 58010041HCID 58010041, compound

Product 1

HCID 86637186HCID 86637186, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclohexyl)methanone (0.720 g, 2.74 mmol), anhydrous hydrazine (0.430 mL, 13.7 mmol) and AcOH (0.025 mL, 0.44 mmol) in EtOH (40 mL) was heated at reflux for about 20 h. During this time, water was removed from the reaction mixture via the use of a Dean-Stark trap. The reaction mixture was cooled to ambient temperature, the volatiles were removed under reduced pressure and the residue was partitioned between water (29 mL) and EtOAc (30 mL). The organic layer was dried over anhydrous MgSO4, filtered, and the solvent evaporated under reduced pressure. The crude material was purified by silica gel chromatography using a gradient of 10 to 50% EtOAc in heptane as the eluent to provide 5-chloro-4-(cyclohexyl(hydrazono)methyl)-1H-pyrrolo[2,3-b]pyridine as an off-white solid (0.37 g, 48%); LC/MS (Table 2, Method o) Rt=2.22 min; MS m/z: 277 and 279 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about 20 h
  3. customDuring this time, water was removed from the reaction mixture via the use of a Dean-Stark trap
  4. customthe volatiles were removed under reduced pressure
  5. customthe residue was partitioned between water (29 mL) and EtOAc (30 mL)
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f588cc4992714633a7c290f5dee6bd67
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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