4-(2-((2-Methoxyethoxy)methoxy)ethoxy)aniline → N-(3-((5-fluoro-2-((4-(2-((2-methoxyethoxy)methoxy)ethoxy)phenyl)amino)pyrimidin-4-yl)(methyl)amino)phenyl)acrylamide

HRID 2274301Notes

Reaction equation

HRID 2274301 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:18])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=2)[C:5]([F:19])=[CH:4][N:3]=1.[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1>>[F:19][C:5]1[C:6]([N:8]([CH3:18])[C:9]2[CH:10]=[C:11]([NH:15][C:30](=[O:29])[CH:31]=[CH2:32])[CH:12]=[CH:13][CH:14]=2)=[N:7][C:2]([NH:34][C:33]2[CH:32]=[CH:31][C:30]([O:29][CH2:28][CH2:27][O:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH3:20])=[CH:36][CH:35]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 867243654-(2-((2-Methoxyethoxy)methoxy)ethoxy)anilineHCID 867243672-chloro-5-fluoro-N-methyl-N-(3-nitrophenyl)pyrimidin-4-amine

Product 1

HCID 86724368N-(3-((5-fluoro-2-((4-(2-((2-methoxyethoxy)methoxy)ethoxy)phenyl)amino)pyrimidin-4-yl)(methyl)amino)phenyl)acrylamide

Procedure

Synthesis of I-24 was performed as described for I-3 (Example 1) using 2-chloro-5-fluoro-N-methyl-N-(3-nitrophenyl)pyrimidin-4-amine in place of 2-chloro-5-fluoro-N-(3-nitrophenyl)pyrimidin-4-amine and 4-(2-((2-methoxyethoxy)methoxy)ethoxy)aniline in place of 4-[(2-methoxyethoxy)methoxy]aniline. M+1=423.9. 1H NMR (DMSO-d6, 400 MHz) 3.44 (s, 3H), 3.664-3.688 (t, 2H, J=4.8), 3.900-3.924 (t, 2H, J=4.8), 5.754-5.779 (d, 1H, J=10), 6.232-6.274 (d, 1H, J=16.8), 6.385-6.453 (m, 2H), 6.810-6.832 (d, 1H, J=8.8), 7.009-7.028 (d, 1H, J=7.6), 7.328-7.368 (t, 1H, J=8), 7.512-7.572 (m, 3H), 7.652 (s, 1H), 7.965-9.978 (d, 1H, J=5.2), 8.196 (s, 1H), 9.120 (s, 1H), 10.245 (s, 1H).

Workup

  1. customSynthesis of I-24

Sources & evidence

ORD record
ord-fe429868337b46899f6445c3bf5dc9d6
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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