N-Methylmaleimide → HCID 56595719, compound

HRID 1668493Notes

Reaction equation

HRID 1668493 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=2)[CH:3]=[CH:2]1.[CH3:19][N:20]1[C:24](=[O:25])[CH:23]=[CH:22][C:21]1=[O:26]>C(O)(=O)C>[CH3:19][N:20]1[C:24](=[O:25])[CH2:23][CH:22]([C:3]2[C:4]3[C:9](=[CH:8][C:7]([NH:10][C:11](=[O:18])[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[C:21]1=[O:26]

Participants

4

Reactant 2

HCID 70261N-MethylmaleimideHCID 67339635HCID 67339635, compound

Product 1

HCID 56595719HCID 56595719, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 114 (3.5 g, 14.813 mmol) and N-methylmaleimide (4.07 g, 37.033 mmol) in glacial acetic acid (100 mL) was refluxed for 56 h. The reaction was brought to room temperature and acetic acid was evaporated. The crude solid was taken into ethyl acetate (100 mL), washed with sat. NaHCO3 solution (3×20 mL), brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (EtOAc: Hexanes, 1:3 to 1:1) to obtain compound 115 (2.32 g, 45%) as a foam. 1H NMR (DMSO-d6) δ 2.80 (dd, 1H, J=5.1, 18.0 Hz), 2.92 (s, 3H), 3.23 (dd, 1H, J=9.3, 18.0 Hz), 4.34 (dd, 1H, J=5.1, 9.3 Hz), 7.26-7.36 (m, 2H), 7.45-7.60 (m, 4H), 7.95-7.98 (m, 2H), 8.07 (s, 1H), 10.17 (s, 1H), 11.02 (s, 1H); ESI-MS (m/z, %) 370 (M+Na, 100), 348 (MH+, 58).

Workup

  1. customwas brought to room temperature
  2. customacetic acid was evaporated
  3. washwashed with sat. NaHCO3 solution (3×20 mL), brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customSolvent was evaporated
  6. customcrude was purified by column chromatography (EtOAc: Hexanes, 1:3 to 1:1)

Sources & evidence

ORD record
ord-0f5ef82a6b8f455c977b9837d739d519
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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