Benzylamine → HCID 22097201, compound

HRID 861523Notes

Reaction equation

HRID 861523 reaction equation
[C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N:16]3[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]3[CH3:22])=[C:12]([Cl:15])[CH:13]=2)[NH:8][C:7](=[O:23])[C:6]1=[O:24])([OH:3])=O.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[CH2:25]([NH:32][C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N:16]3[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]3[CH3:22])=[C:12]([Cl:15])[CH:13]=2)[NH:8][C:7](=[O:23])[C:6]1=[O:24])=[O:3])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22097163HCID 22097163, compound

Product 1

HCID 22097201HCID 22097201, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.3 g (3.7 mmol) of 1-(carboxymethyl)-7-chloro-6-(2,5-dimethyl-1-pyrrolyl)-2,3(1H,4H)-quinoxalinedione and 1.6 ml (12.3 mmol) of benzylamine were dissolved in 30 ml of dimethylformamide and, at 0° C., a solution of 0.89 ml (4.1 mmol) of diphenylphosphoryl azide in 10 ml of dimethylformamide was added dropwise. The mixture was stirred at room temperature for 16 h and then poured into ice-water, and the aqueous phase was extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase: toluene/acetone=1:1) to yield 1.1 g (67%) of the product.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (mobile phase: toluene/acetone=1:1)

Sources & evidence

ORD record
ord-b177e264ea824380b8d6c7a6797b9aa4
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

Loading…