Aminoacetaldehyde dimethyl acetal → HCID 10774499, compound

HRID 1954723Notes

Reaction equation

HRID 1954723 reaction equation
Cl[C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:13])[CH:8]=2)[N:3]=1.CO[CH:16]([O:19]C)[CH2:17][NH2:18]>>[F:13][C:7]1[CH:8]=[C:9]2[C:4]([NH:3][C:16](=[O:19])[C:17]3[N:10]2[CH:11]=[CH:2][N:18]=3)=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 4447681Quinoxaline, 2,3-dichloro-6-fluoro-

Product 1

HCID 10774499HCID 10774499, compound

Procedure

By reacting 2,3-dichloro-6-fluoroquinoxaline with aminoacetaldehyde dimethyl acetal, following a procedure that is similar to that described in example 1, there is obtained 8-fluoroimidazo[1,2-a]quinoxalin-4(5H)-one (m.p. >300° C.) and, subsequently, 4-chloro-8-fluoroimidazo[1,2-]quinoxaline. By reacting this product with cyclopentyl amine according to the method described in example 3, there is obtained 4-cyclopentylamino-8-dichloroimidazo[1,2-a]quinoxaline. m.p. (DSC)=85.7° C.(onset); IR (KBr): 3255, 2964, 1551 cm-1 ; 1H-NMR (CDCl3): δ7.8 (1H,m), 7.7÷7.35 (1H,dd, JHF =16 Hz), 7.5 (1H,d, J=2 Hz), 7.6÷7.25 (1H,dd, JHF =16 Hz), 7.05 (1H,dd), 6.0 (1H,d), 4.55 (1H,m), 2.35÷1.3 (8H,m); UV (EtOH): λmax =226, 268, 285, 296, 323, 336 nm. Elementary analysis for C15H15FN4 (m.w. 270.31): calcd. C 66.65, H 5.59, N 20.73%; found C 66.36, H 5.66, N 20.86%.

Sources & evidence

ORD record
ord-5425cccda5644849adfbe132c0875368
Source dataset
uspto-grants-2000_09
Patent number
US06124287

Reaction notes

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