N,N-Dimethylethylenediamine → N1-(6-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)pyrazin-2-yl)-N2,N2-dimethylethane-1,2-diamine

HRID 455111Notes

Reaction equation

HRID 455111 reaction equation
ClC1C=C[C:5]2[N:6]([C:8](CNC3N=C(N4CCC(C)(O)CC4)C=CN=3)=[C:9](C3C=CC=CC=3)[N:10]=2)[CH:7]=1.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[N:41]=[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]3[C:48]=2[CH2:49][C:50]2[CH:55]=[N:54][CH:53]=[C:52](Cl)[N:51]=2)=[CH:36][CH:35]=1.CN(C)CCN>>[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[N:41]=[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]3[C:48]=2[CH2:49][C:50]2[N:51]=[C:52]([NH:10][CH2:9][CH2:8][N:6]([CH3:7])[CH3:5])[CH:53]=[N:54][CH:55]=2)=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 670290991-(2-((6-Chloro-2-phenylimidazo[1,2-a]pyridin-3-yl)methylamino)pyrimidin-4-yl)-4-methylpiperidin-4-olHCID 866551242-(4-Chlorophenyl)-3-((6-chloropyrazin-2-yl)methyl)imidazo[1,2-a]pyridine

Product 1

HCID 67308371N1-(6-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)pyrazin-2-yl)-N2,N2-dimethylethane-1,2-diamine

Procedure

The title compound was prepared in the same fashion as that described for compound 187 from 2-(4-chlorophenyl)-3-((6-chloropyrazin-2-yl)methyl)imidazo[1,2-a]pyridine and N1,N1-dimethylethane-1,2-diamine. M/e+ 407 for C22H24ClN6 (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.12 (d, J=6.9 Hz, 1H), 7.85 (d, J=8.8 Hz, 2H), 7.78 (s, 1H), 7.63 (d, J=8.4 Hz, 2H), 7.42 (d, J=8.4 Hz, 2H), 7.20 (m, 1H), 6.78 (m, 1H), 5.30 (s, 1H), 4.34 (s, 2H), 3.29 (q, J=5.5 Hz, 2H), 2.46 (t, J=5.5 Hz, 2H), 2.21 (s, 6H) ppm.

Sources & evidence

ORD record
ord-01aa3763eac14504b28b465dbcd13fc3
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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