2-Methoxy-4-[2-(4-methylpiperazin-1-yl)ethyl]aniline → N-(2,6-difluorophenyl)-2-(ethyloxy)-5-{3-[2-({2-(methyloxy)-4-[2-(4-methyl-1-piperazinyl)ethyl]phenyl}amino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-2-yl}benzamide

HRID 419465Notes

Reaction equation

HRID 419465 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:17]2[CH:18]=[CH:19][C:20]([O:34][CH2:35][CH3:36])=[C:21]([CH:33]=2)[C:22]([NH:24][C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=2[F:32])=[O:23])[CH:5]=[CH:4][N:3]=1.[CH3:37][O:38][C:39]1[CH:45]=[C:44]([CH2:46][CH2:47][N:48]2[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]2)[CH:43]=[CH:42][C:40]=1[NH2:41]>>[F:32][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([F:31])[C:25]=1[NH:24][C:22](=[O:23])[C:21]1[CH:33]=[C:17]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]3[C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:41][C:40]3[CH:42]=[CH:43][C:44]([CH2:46][CH2:47][N:48]4[CH2:49][CH2:50][N:51]([CH3:54])[CH2:52][CH2:53]4)=[CH:45][C:39]=3[O:38][CH3:37])[N:7]=2)[CH:18]=[CH:19][C:20]=1[O:34][CH2:35][CH3:36]

Participants

3

Reactant 2

HCID 574161632-Methoxy-4-[2-(4-methylpiperazin-1-yl)ethyl]anilineHCID 594529415-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-(ethyloxy)benzamide

Product 1

HCID 59452790N-(2,6-difluorophenyl)-2-(ethyloxy)-5-{3-[2-({2-(methyloxy)-4-[2-(4-methyl-1-piperazinyl)ethyl]phenyl}amino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-2-yl}benzamideYield 67%

Procedure

The title compound (0.12 g, 0.17 mmol, 67%) was prepared from 5-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-(ethyloxy)benzamide (Intermediate Example 6) and 2-(methyloxy)-4-[2-(4-methyl-1-piperazinyl)ethyl]aniline (Example 131, step D) in an analogous manner to that described for Example 26, step E. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (t, J=6.8 Hz, 3H), 2.10 (s, 3H), 2.28 (br. s., 4H), 2.40 (br. s., 3H), 2.49 (d, J=8.4 Hz, 3H), 2.63-2.72 (m, 2H), 3.79 (s, 3H), 4.23 (q, J=6.9 Hz, 2H), 6.57 (d, J=4.9 Hz, 1H), 6.71-6.79 (m, 1H), 6.91-6.99 (m, 2H), 7.16 (t, J=8.1 Hz, 2H), 7.23 (d, J=9.0 Hz, 1H), 7.30-7.37 (m, 1H), 7.37-7.46 (m, 1H), 7.62 (d, J=7.9 Hz, 1H), 7.64-7.74 (m, 2H), 8.02 (s, 1H), 8.23 (d, J=5.3 Hz, 1H), 8.47 (s, 1H), 9.35 (d, J=6.8 Hz, 1H), 9.71 (s, 1H). MS (M+H, ES+) 720.

Sources & evidence

ORD record
ord-6ed51da5ff0b44c086be984d34b78425
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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