Sodium Chloride → HCID 49793042, compound

HRID 1695470Notes

Reaction equation

HRID 1695470 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12](/[CH:13]=[CH:14]\[C:15]3[CH:16]=[C:17]([C:21](O)=[O:22])[N:18]([CH3:20])[N:19]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[CH:4][CH:3]=1.O.O[N:27]1[C:31]2[CH:32]=CC=C[C:30]=2N=N1.C(N(C(C)C)C(C)C)C.C(N)(C)C.[Cl-].[Na+]>CN(C=O)C>[CH:31]([NH:27][C:21]([C:17]1[N:18]([CH3:20])[N:19]=[C:15](/[CH:14]=[CH:13]\[C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][O:10][C:11]=2[CH3:24])[CH:16]=1)=[O:22])([CH3:32])[CH3:30]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 66643734HCID 66643734, compound

Product 1

HCID 49793042HCID 49793042, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-{(Z)-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl}-2-methyl-2H-pyrazole-3-carboxylic acid (0.3 mmol) in DMF (7 mL) was added 1-hydroxybenzotriazole hydrate (0.45 mmol), N-ethyldiisopropylamine (1.2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidazole hydrochloride 0.45 mmol) and isopropylamine (27.8 mg, 0.45 mmol) and the resulting mixture stirred overnight at room temperature. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution and then dried over sodium sulfate, filtered and evaporated. Concentration and purification by preparative HPLC afforded the title compound (35 mg, 28%) as an off white gum. MS: m/e=369.2 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. concentrationConcentration and purification by preparative HPLC

Sources & evidence

ORD record
ord-838d6bc47b7a47bca4172ae25ec4ef11
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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