N-(Methoxycarbonyl)maleimide → HCID 71230565, compound

HRID 1746282Notes

Reaction equation

HRID 1746282 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[NH:10][NH:9][C:8]1=[O:13].COC(N1[C:22](=[O:23])[CH:21]=[CH:20][C:19]1=[O:24])=O>C([O-])(O)=O.[Na+]>[O:23]=[C:22]1[CH:21]=[CH:20][C:19](=[O:24])[N:2]1[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:8](=[O:13])[NH:9][NH:10][C:11]1=[O:12]

Participants

4

Reactant 2

HCID 580610N-(Methoxycarbonyl)maleimideHCID 712305891418310-93-6

Product 1

HCID 71230565HCID 71230565, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To 4-(4-aminobutyl)-1,2,4-triazolidine-3,5-dione hydrochloride (I-14a: 42 mg, 0.201 mmol) in NaHCO3 sat aqueous solution (1.006 mL) at 0° C. was added N-methoxycarbonylmaleimide (31.2 mg, 0.201 mmol). The mixture was stirred at 0° C. for 1 h, and then at room temperature for 2 h. The mixture was purified by preparative hplc (0-60% CH3CN/(0.1% TFA in H2O)), and then lyophilized, giving 4-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)-1,2,4-triazolidine-3,5-dione (I-14b: 10 mg, 20%) a white solid. LC-MS (M+1) 253.3, t=0.89 minute. 1H NMR (400 MHz, CD3CN) δ ppm 1.51-1.62 (m, 4H) 3.45 (t, J=6.44 Hz, 2H) 3.49 (t, J=6.44 Hz, 2 H) 6.76 (s, 2 H) 7.52 (br. s., 2 H).

Workup

  1. customat 0° C.
  2. waitat room temperature for 2 h
  3. customThe mixture was purified by preparative hplc (0-60% CH3CN/(0.1% TFA in H2O))

Sources & evidence

ORD record
ord-867a0bc41f704415a120b9519ec6bbe4
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

Loading…