Hydrazine hydrate (1:1) → HCID 67227116, compound

HRID 1043220Notes

Reaction equation

HRID 1043220 reaction equation
[C:1]([C:3]1[C:20](F)=[CH:19][CH:18]=[CH:17][C:4]=1[O:5][C:6]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])#[N:2].O.[NH2:23][NH2:24].C(N(C(C)C)C(C)C)C>O1CCOCC1>[NH2:2][C:1]1[C:3]2[C:20](=[CH:19][CH:18]=[CH:17][C:4]=2[O:5][C:6]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:7]=2[C:8]([O:10][CH3:11])=[O:9])[NH:24][N:23]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 67227369HCID 67227369, compound

Product 1

HCID 67227116HCID 67227116, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of EXAMPLE 428A (14.8 g), hydrazine monohydrate (2.74 mL) and N-ethyl-N-isopropylpropan-2-amine (18 mL) in dioxane (150 mL) was heated at 90° C. overnight. The solvent was removed, and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting from 80%-100% ethyl acetate in hexanes to give the title compound.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted with additional ethyl acetate three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel eluting from 80%-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c7d770faa825439b9fb90d915baa0cd6
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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