N-[3-(3-{2-[(3-Chloro-4-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide → 3-Fluoro-4-(2-methoxyethoxy)aniline

HRID 1159934Notes

Reaction equation

HRID 1159934 reaction equation
ClC1C=C(NC2N=C(C3C(C4C=C(NC(=O)C5C(F)=CC=CC=5F)C=CC=4)=NN4C=CC=CC=34)C=CN=2)C=CC=1OCCN(C)C.[F:47][C:48]1[CH:53]=[C:52]([N+:54]([O-])=O)[CH:51]=[CH:50][C:49]=1[O:57][CH2:58][CH2:59][O:60][CH3:61]>>[F:47][C:48]1[CH:53]=[C:52]([NH2:54])[CH:51]=[CH:50][C:49]=1[O:57][CH2:58][CH2:59][O:60][CH3:61]

Participants

3

Reactant 2

HCID 11505567N-[3-(3-{2-[(3-Chloro-4-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamideHCID 234980752-Fluoro-1-(2-methoxyethoxy)-4-nitrobenzene

Product 1

HCID 234981173-Fluoro-4-(2-methoxyethoxy)aniline

Procedure

In a procedure analogous to Example 125, 250 mg of the title compound was prepared from 2-fluoro-1-{[2-(methyloxy)ethyl]oxy}-4-nitrobenzene as brown oil. 1H NMR (CDCl3, 400 MHz) δ 3.40 (s, 3H), 3.51 (brs, 2H), 3.67 (d, 2H, J=4.7 Hz), 4.06 (t, 2H, J=4.7 Hz), 6.32 (d, 1H, J=8.6 Hz), 6.41 (dd, 1H, J=12.6 and 2.8 Hz), and 6.8 (t, 1H, J=9.0 Hz).

Sources & evidence

ORD record
ord-f5fdc1a8b42d4988bd9df19aff59cc86
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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