Hydrazine → HCID 68992711, compound

HRID 657156Notes

Reaction equation

HRID 657156 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][N:7]([CH2:9][CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[N:14][C:13]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[N:21][C:12]2=3)[CH2:6][CH:5]([CH2:24][N:25]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:4]1.NN>CCO>[NH2:25][CH2:24][C@H:5]1[CH2:4][C@@H:3]([O:2][CH3:1])[CH2:8][N:7]([CH2:9][CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[N:14][C:13]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[N:21][C:12]2=3)[CH2:6]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 68993740HCID 68993740, compound

Product 1

HCID 68992711HCID 68992711, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To 2-[((3RS,5SR)-5-(methyloxy) 1-{2-[6-(methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]ethyl}-3-piperidinyl)methyl]-1H-isoindole-1,3(2H)-dione (110 mg, 0.23 mmol) in EtOH (5 mL) was added anhydrous hydrazine (0.5 mL, 15.0 mmol). The reaction was warmed to 40° C. and allowed to stir under nitrogen for 24 h. The reaction was filtered through a pad of Celite® and the filtrate was partitioned between EtOAc (50 mL) and water (10 mL). The aqueous layer was further extracted with EtOAc (2×25 mL), and the combined organic layers were dried over Na2SO4. The solvents were removed to provide the desired compound (62 mg; 77%) as a tan solid which was used without further purification.

Workup

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. customthe filtrate was partitioned between EtOAc (50 mL) and water (10 mL)
  3. extractionThe aqueous layer was further extracted with EtOAc (2×25 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. customThe solvents were removed

Sources & evidence

ORD record
ord-beef936dd91b45bb9eef13936e850d08
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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