Trifluoroacetic anhydride → 2-(5-Fluorobenzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrile

HRID 1405323Notes

Reaction equation

HRID 1405323 reaction equation
C([NH:5][C:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([C:18]1[O:19][C:20]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:21]=3[CH:22]=1)[C:12]([N:28]([CH3:32])[CH:29]([CH3:31])[CH3:30])=[N:11]2)=O)(C)(C)C.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>ClCCl>[F:27][C:24]1[CH:25]=[CH:26][C:20]2[O:19][C:18]([C:13]3[C:12]([N:28]([CH3:32])[CH:29]([CH3:31])[CH3:30])=[N:11][C:10]4[C:15](=[CH:16][CH:17]=[C:8]([C:6]#[N:5])[CH:9]=4)[N:14]=3)=[CH:22][C:21]=2[CH:23]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 70654245N-tert-butyl-2-(5-fluorobenzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxamide

Product 1

HCID 706542402-(5-Fluorobenzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrileYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butyl-2-(5-fluorobenzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxamide (600 mg, crude) in dichloromethane (30 ml) was added TFAA (3 ml) with stifling overnight at room temperature. The reaction mixture was quenched with water (80 ml) and adjusted to pH 8 with sodium bicarbonate solution, extracted with dichloromethane (4×50 ml), and the organic layers combined and concentrated in vacuo to give the residue, which was purified by silica gel column chromatography (1% ethyl acetate in petroleum ether) to afford 2-(5-fluorobenzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrile as a yellow solid (400 mg, 80%).

Workup

  1. customThe reaction mixture was quenched with water (80 ml)
  2. extractionextracted with dichloromethane (4×50 ml)
  3. concentrationconcentrated in vacuo
  4. customto give the residue, which
  5. customwas purified by silica gel column chromatography (1% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-12e996572abe4657be0038df064c2c26
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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