Cyclohexylamine → 4-Cyclohexylamino-1-methyl imidazo [1,2-a]quinoxaline

HRID 1954711Notes

Reaction equation

HRID 1954711 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[C:12]([NH:13][C:14](=O)[C:5]2=[N:4][CH:3]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>>[CH:16]1([NH:22][C:14]2[C:5]3[N:6]([C:2]([CH3:1])=[CH:3][N:4]=3)[C:7]3[C:12]([N:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 107743711-methylimidazo[1,2-a]quinoxaline-4(5H)-one

Product 1

HCID 105647244-Cyclohexylamino-1-methyl imidazo [1,2-a]quinoxaline

Procedure

By reaction of 1-methylimidazo[1,2-a]quinoxaline-4(5H)-one (example 2) with cyclohexylamine, according to a procedure that is similar to that followed in example 9, there is obtained 4-cyclohexylamino-1-methyl imidazo [1,2-a]quinoxaline. m.p. (DSC)=126.5° C. (onset); IR (KBr): 3345, 2938, 1546 cm-1 ; 1H-NMR (CDCl3): δ8.0 (1H,dd), 7.7 (1H,dd), 7.5÷7.1 (3H,m), 6.0 (1H,d), 4.2 (1H,m), 2.85 (3H,s), 2.3÷1.95 (4H,m), 1.95÷0.9 (6H,m); UV (EtOH): λmax =225, 243, 272, 301, 316, 329 nm. Elementary analysis for C17H20N4 (m.w.280.37): calcd. C 72.83, H 7.19, N 19.98%; found C 72.21, H 7.54, N 20.14%.

Sources & evidence

ORD record
ord-c99f0564b71a47fbb32187705e871b36
Source dataset
uspto-grants-2000_09
Patent number
US06124287

Reaction notes

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