Triethylamine → HCID 22054163, compound

HRID 1830433Notes

Reaction equation

HRID 1830433 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:30][O:31][C:32]1[C:33](=[O:56])[C:34]([CH3:55])=[C:35]([CH2:41][C:42]2[CH:43]=[CH:44][C:45]([O:51][C:52](=[O:54])[CH3:53])=[C:46]([CH:50]=2)[C:47](O)=[O:48])[C:36](=[O:40])[C:37]=1[O:38][CH3:39]>C(Cl)Cl>[O:11]1[CH2:10][CH2:9][N:8]([C:5]2[N:4]=[CH:3][C:2]([NH:1][C:47](=[O:48])[C:46]3[CH:50]=[C:42]([CH2:41][C:35]4[C:36](=[O:40])[C:37]([O:38][CH3:39])=[C:32]([O:31][CH3:30])[C:33](=[O:56])[C:34]=4[CH3:55])[CH:43]=[CH:44][C:45]=3[O:51][C:52](=[O:54])[CH3:53])=[CH:7][CH:6]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1040596-(Morpholino)pyridin-3-amineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 220542715-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic Acid

Product 1

HCID 22054163HCID 22054163, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-6-morpholinopyridine (0.269 g, 1.500 mmol), triethylamine (0.197 g, 1.950 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.165 g, 0.975 mmol) were added to a methylene chloride solution (100 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.281 g, 0.750 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1) to obtain the titled compound (0.239 g, 0.446 mmol, 59%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-73dfd33a61c046faab0e972a24963b02
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

Loading…