Diisopropylethylamine → 2-chloro-N-(3-(quinoxalin-2-yl)phenyl)propanamide

HRID 2045930Notes

Reaction equation

HRID 2045930 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.C(N(C(C)C)CC)(C)C.[Cl:27][CH:28]([CH3:32])[C:29](Cl)=[O:30]>C1COCC1.C(OCC)(=O)C>[Cl:27][CH:28]([CH3:32])[C:29]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)=[O:30]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1110192-Chloropropionyl chlorideHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 582003822-chloro-N-(3-(quinoxalin-2-yl)phenyl)propanamideYield 52.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (124 mg, 0.560 mmol) and diisopropylethylamine (DIEA, 111 μL, 0.672 mmol) in THF (5 mL), 2-chloropropionyl chloride (60 μL, 0.620 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 24 hrs and then diluted with ethyl acetate (20 mL). The organic phase was washed with water (20 mL), dried over MgSO4 and the solvent was evaporated in vacuo to afford 2-chloro-N-(3-(quinoxalin-2-yl)phenyl)propanamide (92 mg, 52% yield). LCMS calculated for C17H14ClN3O (M+H): 312.77. found 313. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.52 (1H, br.), 9.53 (1H, s), 8.55 m), 8.12-8.18 (2H, m), 8.05-8.08 (1H, m), 7.82-7.95 (3H, m), 7.55-7.60 (1H, m), 4.75 (1H, q, J=6.8 Hz), 1.68 (3H, d, J=6.8 Hz).

Workup

  1. washThe organic phase was washed with water (20 mL)
  2. dry with materialdried over MgSO4
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b4c9fd160ff64e519349a304e6476626
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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