Hydrazine hydrate (1:1) → HCID 11757210, compound

HRID 1623048Notes

Reaction equation

HRID 1623048 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([NH:20][CH:21]([CH2:26][N:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[C:22]([O:24][CH3:25])=O)=[O:19])=[CH:13][CH:12]=3)[CH:6]=[CH:5][N:4]=1.[OH2:40].[NH2:41][NH2:42]>CO>[O:40]=[C:25]1[O:24][C:22]([C@@H:21]([NH:20][C:18]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([NH:2][CH3:1])[N:8]=2)=[CH:17]3)=[O:19])[CH2:26][N:27]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[N:42][NH:41]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 67504735HCID 67504735, compound

Product 1

HCID 11757210HCID 11757210, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

1.78 g (3.4 mmol) of ester 32 were dissolved in 30 ml of MeOH. 0.83 ml of hydrazine hydrate was added and the mixture was stirred at 40° C. for 5 h. After that, a further 1.6 ml of hydrazine hydrate were added and the mixture was stirred at RT for 15 h. The solvents were removed i.v. and the residue was taken up in 80 ml of dichloromethane. 3.2 ml of a 20% solution of phosgene in toluene were added and the mixture was stirred for 3 days. After that, the solvent was removed i.v. and the residue was partitioned between 80 ml of water and 80 ml of ethyl acetate. When this was done, a solid precipitated out and was filtered off with suction. The organic phase was evaporated and the residue was combined with the solid and chromatographed on silica gel using heptane/ethyl acetate 1:5. 390 mg (21%) of the oxadiazolone 33 was obtained. Empirical formula C29H25N9O3; M.W.=547.58; MS (M+H) 548.2.

Workup

  1. stirringthe mixture was stirred at RT for 15 h
  2. customThe solvents were removed i.v
  3. addition3.2 ml of a 20% solution of phosgene in toluene were added
  4. stirringthe mixture was stirred for 3 days
  5. customAfter that, the solvent was removed i.v
  6. customand the residue was partitioned between 80 ml of water and 80 ml of ethyl acetate
  7. customa solid precipitated out and
  8. filtrationwas filtered off with suction
  9. customThe organic phase was evaporated
  10. customchromatographed on silica gel

Sources & evidence

ORD record
ord-2a92fb7e6eb64b4f88fce52206fb5a8c
Source dataset
uspto-grants-2014_07
Patent number
US08778955B2

Reaction notes

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