3-(2-Morpholin-4-ylethoxy)aniline → 2,6-Difluoro-N-[3-(3-{2-[(3-{[2-(4-morpholinyl)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]benzamide

HRID 1159894Notes

Reaction equation

HRID 1159894 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:18]1[N:23]=[C:22]([C:24]2[C:25]([C:33]3[CH:34]=[C:35]([NH:39][C:40](=[O:49])[C:41]4[C:46]([F:47])=[CH:45][CH:44]=[CH:43][C:42]=4[F:48])[CH:36]=[CH:37][CH:38]=3)=[N:26][N:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=23)[CH:21]=[CH:20][N:19]=1>>[F:48][C:42]1[CH:43]=[CH:44][CH:45]=[C:46]([F:47])[C:41]=1[C:40]([NH:39][C:35]1[CH:36]=[CH:37][CH:38]=[C:33]([C:25]2[C:24]([C:22]3[CH:21]=[CH:20][N:19]=[C:18]([NH:16][C:12]4[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:8][CH2:7][N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)[CH:11]=4)[N:23]=3)=[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][N:27]3[N:26]=2)[CH:34]=1)=[O:49]

Participants

3

Reactant 2

HCID 64866163-(2-Morpholin-4-ylethoxy)anilineHCID 59513803N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide

Product 1

HCID 595137002,6-Difluoro-N-[3-(3-{2-[(3-{[2-(4-morpholinyl)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]benzamide

Procedure

The title compound was prepared from (3-{[2-(4-morpholinyl)ethyl]oxy}phenyl)-amine and N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide in a manner analogous to Example 27, Step D. 1H NMR (400 MHz, DMSO-d6) δ 10.94 (s, 1H), 9.55 (s, 1H), 8.84 (d, 1H), 8.48 (d, 1H), 8.27 (d, 1H), 8.01 (s, 1H), 7.81 (d, 1H), 7.59 (m, 1H), 7.49 (m, 3H), 7.35 (d, 1H), 7.25 (m, 3H), 7.13 (t, 2H), 6.51 (d, 2H), 4.0 (m, 2H), 3.54 (m, 4H), 2.64 (m, 2H), 2.41 (m, 4H). HRMS calculated C36H32F2N7O3 [M+H]+ 648.2535, found 648.2528.

Sources & evidence

ORD record
ord-21ba7d1a4cdf490d85fec71ff6bf7c30
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

Loading…