Benzylamine → 1-Benzylcarbamoylmethyl-7-(1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

HRID 861483Notes

Reaction equation

HRID 861483 reaction equation
[C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:20]([F:23])([F:22])[F:21])=[C:12]([N:15]3[CH:19]=[CH:18][CH:17]=[CH:16]3)[CH:13]=2)[NH:8][C:7](=[O:24])[C:6]1=[O:25])([OH:3])=O.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[CH2:26]([NH:33][C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:20]([F:23])([F:22])[F:21])=[C:12]([N:15]3[CH:19]=[CH:18][CH:17]=[CH:16]3)[CH:13]=2)[NH:8][C:7](=[O:24])[C:6]1=[O:25])=[O:3])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 102474741-(Carboxymethyl)-7-(1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

Product 1

HCID 220971491-Benzylcarbamoylmethyl-7-(1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedioneYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2.0 g (6.5 mmol) of 1-carboxymethyl-7-(1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione and 0.64 g (5.9 mmol) of benzylamine were dissolved in 50 ml of anhydrous dimethylformamide. At 0° C., 1.6 g (5.9 mmol) of diphenylphosphoryl azide dissolved in a little dimethylformamide, and 1.3 g (12.5 mmol) of triethylamine were successively added dropwise. The mixture was stirred at room temperature for 4 h and then poured into water buffered with sodium bicarbonate. The resulting precipitate was filtered off with suction to yield 1.6 g (62%) of the product. Melting point 241°-242° C.

Workup

  1. additionwere successively added dropwise
  2. filtrationThe resulting precipitate was filtered off with suction

Sources & evidence

ORD record
ord-3dc792eb377d4f138dc9810b88999d75
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

Loading…