Acetic Acid → HCID 76829309, compound

HRID 1969686Notes

Reaction equation

HRID 1969686 reaction equation
[Cl:1][C:2]1[C:3]([C:21](=O)[CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.[NH2:37][NH2:38].CC(O)=O>CCO>[Cl:1][C:2]1[C:3]([C:21](=[N:37][NH2:38])[CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[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 58557552HCID 58557552, compound

Product 1

HCID 76829309HCID 76829309, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of tert-butyl 4-(2-(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-oxoethyl)piperidine-1-carboxylate (1.00 g, 1.87 mmol) in EtOH (6.4 mL) were added anhydrous hydrazine (2.94 mL, 94.0 mmol) and AcOH (0.536 mL, 9.36 mmol). The reaction mixture was stirred at reflux for about 16 h. The solvent was removed under reduced pressure and the crude material was taken up in DCM and dried over anhydrous MgSO4. The solvent was removed and DCM (3 mL) was added. The solid was removed by filtration and the filtrate was purified by silica gel chromatography eluting with 0-10% MeOH in DCM to afford tert-butyl 4-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-hydrazonoethyl)piperidine-1-carboxylate (0.324 g, 44%) as a white solid consisting of a 1/1 mixture of E/Z isomers: LC/MS (Table 1, Method r) Rt=1.46 and 1.53 min; MS m/z: 392/394 and 392/394 (M+H)+.

Workup

  1. temperatureat reflux for about 16 h
  2. customThe solvent was removed under reduced pressure
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was removed
  5. additionDCM (3 mL) was added
  6. customThe solid was removed by filtration
  7. customthe filtrate was purified by silica gel chromatography
  8. washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-843760abece543ae9643abc9d459413b
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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