Methylamine → HCID 15291207, compound

HRID 374759Notes

Reaction equation

HRID 374759 reaction equation
C(O[C:5]1[C:8](=[O:9])[C:7](=[O:10])[C:6]=1[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[N:22])[CH:19]=2)[O:14][C:13]([CH3:24])([CH3:23])[CH:12]=1)(C)C.[CH3:25][NH2:26]>CC#N.CCO>[CH3:24][C:13]1([CH3:23])[CH:12]=[C:11]([C:6]2[C:7](=[O:10])[C:8](=[O:9])[C:5]=2[NH:26][CH3:25])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[N:22])[CH:19]=2)[O:14]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 15291206HCID 15291206, compound

Product 1

HCID 15291207HCID 15291207, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 437 mg (1.35 mmol) of 4-(2-isopropoxy-3,4-dioxo-cyclobut-1-enyl)-2,2-dimethyl-2H-chromene-6-carbonitrile in CH3CN 14 mL) was added dropwise 8.03M methylamine in EtOH. The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was quenched with H2O (50 mL) and then was extracted into 20% THF-CH2Cl2. The combined organic extracts were dried (Na2SO4) and purified by flash chromatography (4% MeOH--CHCl3) and crystallization from CH2Cl2 -petroleum ether to give 210 mg (53% yield) of the title compound, mp 193°-194° C., as a white solid: 1H-NMR (DMSO-d6 ; 400 MHz; major rotamer) δ8.7-8.8 (br q, 1H), 7.78 (d, 1H), 7.67 (dd, 1H), 7.01 (d, 1H), 6.22 (s, 1H), 3.25 (d, 3H), and 1.46 ppm (s, 3H); IR (KBr) 2220, 1775, 1735, 1620 cm-1 ; mass spectrum (DCI+), m/e 2.95.

Workup

  1. customThe reaction mixture was quenched with H2O (50 mL)
  2. extractionwas extracted into 20% THF-CH2Cl2
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. custompurified by flash chromatography (4% MeOH--CHCl3) and crystallization from CH2Cl2 -petroleum ether

Sources & evidence

ORD record
ord-cd230a5ac4e54a5ba5bbc3b7eb1455c5
Source dataset
uspto-grants-1996_01
Patent number
US05482942

Reaction notes

Loading…