Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1) → N-[3-(3-{2-[(3-Chloro-4-{[2-(methyloxy)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[C:17]([C:25]4[CH:26]=[C:27]([NH:31][C:32](=[O:41])[C:33]5[C:38]([F:39])=[CH:37][CH:36]=[CH:35][C:34]=5[F:40])[CH:28]=[CH:29][CH:30]=4)=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=34)[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl.ClCCN1C[CH2:50][O:49][CH2:48][CH2:47]1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[C:17]([C:25]4[CH:26]=[C:27]([NH:31][C:32](=[O:41])[C:33]5[C:38]([F:39])=[CH:37][CH:36]=[CH:35][C:34]=5[F:40])[CH:28]=[CH:29][CH:30]=4)=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=34)[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:47][CH2:48][O:49][CH3:50]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from N-[3-(3-{2-[(3-chloro-4-hydroxyphenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide and 4-(2-chloroethyl)morpholine hydrochloride in a manner analogous to Example 126. 1H NMR (300 MHz, DMSO-d6): δ 10.92 (s, 1H), 9.53 (s, 1H), 8.83 (d, 1H), 8.43 (d, 1H), 8.25 (d, 1H), 8.00 (s, 1H), 7.93 (m, 1H), 7.80 (d, 1H), 7.58 (m, 1H), 7.54-7.44 (m, 3H), 7.33 (d, 1H), 7.24 (m, 2H), 7.11 (m, 1H), 7.05 (d, 1H), 6.52 (d, 1H), 4.10 (m, 2H), 3.55 (m, 4H), 2.69 (m, 2H), 2.48 (m, 4H); HRMS: calc. C36H31N7O3F2 (M+H)+ 682.2145 found 682.2153.
Sources & evidence
- ORD record
- ord-850fffe262594ca4badb63c38e3b3e07
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812022B2
Reaction notes
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