Diisopropylamine → furan-2-carboxylic acid N'-[2-(5-fluoro-2'-trifluoromethoxy-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide

HRID 2250928Notes

Reaction equation

HRID 2250928 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][C:21](O)=[O:22])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][C:15]([F:18])([F:17])[F:16])[CH:7]=1.[CH:24]([NH:27][NH:28][C:29]([C:31]1[O:32][CH:33]=[CH:34][CH:35]=1)=[O:30])([CH3:26])[CH3:25].C(NC(C)C)(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:19][CH2:20][C:21]([N:27]([CH:24]([CH3:26])[CH3:25])[NH:28][C:29]([C:31]2[O:32][CH:33]=[CH:34][CH:35]=2)=[O:30])=[O:22])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][C:15]([F:16])([F:17])[F:18])[CH:7]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 468639N'-isopropylfuran-2-carbohydrazideHCID 2733179PyBroPHCID 58689904(5-Fluoro-2'-trifluoromethoxy-biphenyl-2-yloxy)-acetic acid

Product 1

HCID 11554779furan-2-carboxylic acid N'-[2-(5-fluoro-2'-trifluoromethoxy-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazideYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (5-fluoro-2′-trifluoromethoxy-biphenyl-2-yloxy)-acetic acid (174 mg, 0.52 mmol) and furan-2-carboxylic acid N′-isopropyl-hydrazide (90 mg, 0.53 mmol) in DMF (5 ml) was treated with diisopropyl amine (0.235 ml, 1.32 mmol) and PyBroP (370 mg, 0.79 mmol) at room temperature overnight. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic layer was successively washed with water 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 30-80% ethyl acetate in hexanes gradient to afford the product as a white solid (110 mg, 44%). MS m/e 481.38 (M+H+)

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  2. washThe organic layer was successively washed with water 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 30-80% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-3d1e97738c7743b18edb0e84c68f737c
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Reaction notes

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