1-Benzoyl-2-isopropylhydrazine → Benzoic acid N'-[3-(5-fluoro-2-propoxy-phenyl)-propionyl]-N'-isopropyl-hydrazide

HRID 1724159Notes

Reaction equation

HRID 1724159 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH2:15][CH3:16])=[C:6]([CH2:8][CH2:9][C:10]([OH:12])=O)[CH:7]=1.[CH:17]([NH:20][NH:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:19])[CH3:18].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH2:15][CH3:16])=[C:6]([CH2:8][CH2:9][C:10]([N:20]([CH:17]([CH3:19])[CH3:18])[NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:12])[CH:7]=1

Participants

6

Reactant 4

HCID 188691-Benzoyl-2-isopropylhydrazineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 687991413-(5-Fluoro-2-propoxy-phenyl)-propionic acid

Product 1

HCID 57560120Benzoic acid N'-[3-(5-fluoro-2-propoxy-phenyl)-propionyl]-N'-isopropyl-hydrazideYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(5-fluoro-2-propoxy-phenyl)-propionic acid (160 mg, 0.71 mmoles) and benzoic acid N′-isopropyl-hydrazide (106 mg, 0.60 mmoles) in DMF (3 mL) was treated with diisopropylethylamine (0.26 mL, 1.49 mmoles), and PyBroP (416 mg, 0.89 mmoles) at room temperature for 16 h. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, then dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-50% ethyl acetate/hexanes gradient to afford the product as a solid (84 mg, 30%). LC-MS m/e 387.26 (M+H+)

Workup

  1. customThe reaction mixture was partitioned between 1N HCl and ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 20-50% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-bcc4b4ebbdbe46da8d0f508983d5f610
Source dataset
uspto-grants-2009_02
Patent number
US07485752B2

Reaction notes

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