Tetrahydrofuran → HCID 46917073, compound

HRID 2045915Notes

Reaction equation

HRID 2045915 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.CCN(C(C)C)C(C)C.[Cl:27]CCC(Cl)=O.[CH2:33]1[CH2:37][O:36][CH2:35][CH2:34]1>C(OCC)(=O)C>[Cl:27][CH2:35][CH2:34][CH2:33][C:37]([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:36]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 693643-Chloropropionyl chlorideHCID 81531DiisopropylethylamineHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 46917073HCID 46917073, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (128 mg, 0.578 mmol) and DIEA (115 μL, 0.694 mmol) in THF (5 mL), 3-chloropropionyl chloride (61 μL, 0.636 mmol) was added and the mixture was stirred at room temperature for 48 hrs. The reaction mixture was diluted with ethyl acetate (20 mL), the organic phase was washed with water (10 mL) and then brine (10 mL), dried over MgSO4, and the solvent evaporated in vacuo to afford a light yellow solid. The light yellow solid was triturated with diethyl ether, dried and submitted to preparative LCMS for further purification, to afford 4-chloro-N-[3-(quinoxalin-2-yl)phenyl]butanamide (50 mg, 26% yield). LCMS calculated for C18H16ClN3O (M+H): 326.79. found 326.00. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.20 (1H, br. S), 9.50 (1H, s), 8.55 (1H, m), 8.20-8.15 (2H, m), 8.04 (1H, m), 7.95-7.85 (m, 3H), 7.54 (1H, m), 3.62 (2H, t, 0.1=7 Hz), 2.60 (2H, m), 2.1 (2H, m).

Workup

  1. washthe organic phase was washed with water (10 mL)
  2. dry with materialbrine (10 mL), dried over MgSO4
  3. customthe solvent evaporated in vacuo
  4. customto afford a light yellow solid
  5. customThe light yellow solid was triturated with diethyl ether
  6. customdried
  7. customfor further purification

Sources & evidence

ORD record
ord-c9abdb8f1d004880a37a9c378beca735
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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