Hydrazine → HCID 59472955, compound

HRID 1678782Notes

Reaction equation

HRID 1678782 reaction equation
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:6]([C:12]1[CH:26]=[CH:25][C:15]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:14][CH:13]=1)=[N:7]2.[NH2:33][NH2:34]>O1CCOCC1>[NH:33]([C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:6]([C:12]1[CH:26]=[CH:25][C:15]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:14][CH:13]=1)=[N:7]2)[NH2:34]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58524335HCID 58524335, compound

Product 1

HCID 59472955HCID 59472955, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 16-1 (6.8 g, 15.2 mMol) in anhydrous 1,4-dioxane (20 mL) was added hydrazine (10.8 mL, 343 mMol). The solution was heated to 100° C. in a microwave reactor for 5 minutes. The solvent was removed in vacuo and the crude residue was taken up in ethyl acetate and washed with aqueous NaHCO3 solution followed by brine. The organic layer was dried with MgSO4, filtered and concentrated in vacuo to yield 16-2 as an orange solid. LC/MS (M+1) calculated: 442.5; observed: 442.2

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with aqueous NaHCO3 solution
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5e971be14ef40b6ab3ac2523fd1d12d
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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