Aminoacetaldehyde dimethyl acetal → HCID 10037930, compound

HRID 1954721Notes

Reaction equation

HRID 1954721 reaction equation
Cl[C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:14])=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.CO[CH:17]([O:20]C)[CH2:18][NH2:19]>>[Cl:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[Cl:14])[N:3]1[CH:2]=[CH:11][N:19]=[C:18]1[C:17](=[O:20])[NH:10]2

Participants

3

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 40971682,3,6,7-Tetrachloroquinoxaline

Product 1

HCID 10037930HCID 10037930, compound

Procedure

By reacting 2,3,6,7-tetrachloroquinoxaline with aminoacetaldehyde dimethyl acetal, following a procedure that is similar to that described in example 1, there is obtained 7,8-dichloroimidazo[1,2-a]quinoxalin-4(5H)-one (m.p. >300° C.). By reacting this product with cyclopentylamine according to the method described in example 3, there is obtained 4-cyclopentylamino-7,8-dichloroimidazo[1,2-a]quinoxaline. m.p. (DSC)=139.4° C.(onset); IR (KBr): 3247, 2961, 1589, 1556 cm-1 ; 1H-NMR (CDCl3): δ7.8 (2H,m), 7.7 (1H,s), 7.55 (1H,s), 6.2 (1H,d), 4.6 (1H,m), 2.4÷1.3 (8H,m); UV (EtOH): λmax =235, 274, 292, 304, 330, 345 nm. Elementary analysis for C15H14Cl2N4 (m.w. 321.21): calcd. C 56.09, H 4.39, N 17.44%; found C 56.13, H 4.41, N 17.52%.

Sources & evidence

ORD record
ord-2f1b1ee3e8f341bab64be82f48addb02
Source dataset
uspto-grants-2000_09
Patent number
US06124287

Reaction notes

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