N-[3-(3-{2-[{3-[(4-Amino-2-fluorophenyl)oxy]propyl}(methyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide → 3-Fluoro-4-[2-(1-piperidinyl)ethoxy]phenylamine

HRID 1159937Notes

Reaction equation

HRID 1159937 reaction equation
NC1C=CC(OCCCN(C)C2N=C(C3C(C4C=C(NC(=O)C5C(F)=CC=CC=5F)C=CC=4)=NN4C=CC=CC=34)C=CN=2)=C(F)C=1.[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][N:60]1[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1>>[F:47][C:48]1[CH:53]=[C:52]([CH:51]=[CH:50][C:49]=1[O:57][CH2:58][CH2:59][N:60]1[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1)[NH2:54]

Participants

3

Reactant 2

HCID 59513855N-[3-(3-{2-[{3-[(4-Amino-2-fluorophenyl)oxy]propyl}(methyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamideHCID 595138651-[2-(2-Fluoro-4-nitrophenoxy)ethyl]piperidine

Product 1

HCID 196272493-Fluoro-4-[2-(1-piperidinyl)ethoxy]phenylamine

Procedure

In a manner analogous to Example 125, 0.57 g of the title compound was prepared from 1-{2-[(2-fluoro-4-nitrophenyl)oxy]ethyl}piperidine as a brown oil: 1H NMR (CDCl3, 400 MHz) δ 1.44-1.46 (m, 2H), 1.57-1.63 (m, 4H), 2.50-2.57 (m, 4H), 2.74 (t, 2H, J=6.2 Hz), 3.50 (brs, 2H), 4.08 (t, 2H, J=6.2 Hz), 6.35 (ddd, 1H, J=8.6, 2.5, and 1.5 Hz), 6.45 (dd, 1H, J=12.7 and 2.8 Hz), and 6.81 (t, 1H, J=8.8 Hz).

Sources & evidence

ORD record
ord-31cba8b349fa48329330f19b37d26a45
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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