Acetic Acid → HCID 86637187, compound

HRID 2204637Notes

Reaction equation

HRID 2204637 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[C:18]3[N:23]([Si](C(C)C)(C(C)C)C(C)C)[CH:24]=[CH:25][C:17]=23)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:36][NH2:37].CC(O)=O>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[N:36][NH2:37])[C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[C:18]3[NH:23][CH:24]=[CH:25][C:17]=23)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 58010077HCID 58010077, compound

Product 1

HCID 86637187HCID 86637187, compoundYield 64%

Procedure

The mixture of (1-benzylpiperidin-4-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone (1.85 g, 3.63 mmol), anhydrous hydrazine (0.341 mL, 10.9 mmol) and AcOH (0.21 mL, 3.63 mmol) was heated at reflux over 3 Å molecular sieves in a Dean-Stark trap for about 48 h. The reaction mixture was cooled to ambient temperatures, the solvent was removed under reduced pressure and the residue partitioned between saturated NaHCO3 (100 mL) and EtOAc (100 mL). The organic layer was separated, washed with brine (100 mL), dried in vacuo over anhydrous MgSO4 and concentrated. The residue was suspended in Et2O (15 mL) and the resulting precipitate was collected by filtration and dried in vacuo to yield 4-((1-benzylpiperidin-4-yl)(hydrazono)methyl)-5-chloro-1H-pyrrolo[2,3-b]pyridine (0.85 g, 64%) as an off-white solid: LC/MS (Table 2, Method n) Rt=1.48 min; MS m/z: 368 and 370 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux over 3 Å molecular sieves in a Dean-Stark trap for about 48 h
  3. temperatureThe reaction mixture was cooled to ambient temperatures
  4. customthe solvent was removed under reduced pressure
  5. customthe residue partitioned between saturated NaHCO3 (100 mL) and EtOAc (100 mL)
  6. customThe organic layer was separated
  7. washwashed with brine (100 mL)
  8. dry with materialdried in vacuo over anhydrous MgSO4
  9. concentrationconcentrated
  10. filtrationthe resulting precipitate was collected by filtration
  11. customdried in vacuo

Sources & evidence

ORD record
ord-81b2a40c62a64e33a5edbf129c8a0953
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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