HCID 86754511, compound → HCID 86754512, compound

HRID 618785Notes

Reaction equation

HRID 618785 reaction equation
C(OC(=O)[C:7]([C:30]#[N:31])=[C:8]([NH:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=1)[NH:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])(C)(C)C>C(Cl)Cl>[F:23][C:22]([F:24])([F:25])[C:20]1[CH:21]=[C:16]([NH:15][C:8]([NH:9][CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])=[CH:7][C:30]#[N:31])[CH:17]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:19]=1

Participants

3

Reactant 1

HCID 86754511HCID 86754511, compound

Product 1

HCID 86754512HCID 86754512, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3,5-bis(trifluoromethyl)phenylamino]-2-cyano-3-(3-methylbutylamino)acrylic acid tert-butyl ester (194 mg, 0.417 mmol) in DCM (2 mL) trifluoroacetic acid (2 mL) was added. After 30 min at room temperature the solution was concentrated, the residue was redissolved in carbon tetrachloride (10 mL) and reconcentrated. The product was purified by flash chromatography (6 g silica gel, gradient of heptane/ethyl acetate). 45 mg (30%) of the title compound was obtained as an oil. LCMS: MH+ =366. This compound was identical by LCMS to the product obtained from solid-phase synthesis.

Workup

  1. concentrationAfter 30 min at room temperature the solution was concentrated
  2. dissolutionthe residue was redissolved in carbon tetrachloride (10 mL)
  3. customThe product was purified by flash chromatography (6 g silica gel, gradient of heptane/ethyl acetate)

Sources & evidence

ORD record
ord-a4d679e7314c48a0b84b737895894ba3
Source dataset
uspto-grants-1999_09
Patent number
US05955548

Reaction notes

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