4-(3-Fluorobenzyloxy)-3-methoxyphenylamine → 2-{[4-({4-[(3-fluorobenzyl)oxy]-3-methoxyphenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethanol

HRID 550414Notes

Reaction equation

HRID 550414 reaction equation
[C:1]([C:3]1[C:4]([O:13][CH2:14][CH2:15][OH:16])=[N:5][NH:6][C:7]=1[N:8]=[CH:9][N:10](C)C)#[N:2].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1)N>>[F:34][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=1)[CH2:27][O:26][C:25]1[CH:24]=[CH:23][C:21]([NH:2][C:1]2[N:10]=[CH:9][N:8]=[C:7]3[NH:6][N:5]=[C:4]([O:13][CH2:14][CH2:15][OH:16])[C:3]=23)=[CH:20][C:19]=1[O:18][CH3:17]

Participants

3

Reactant 2

HCID 219519524-(3-Fluorobenzyloxy)-3-methoxyphenylamineHCID 67020529N'-[4-cyano-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-N,N-dimethylimidoformamide

Product 1

HCID 116404512-{[4-({4-[(3-fluorobenzyl)oxy]-3-methoxyphenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethanolYield 54%

Procedure

The procedure described in Example 1 was repeated using N′-[4-cyano-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-N,N-dimethylimidoformamide (2.0 g, 8.96 mmol) and 3-methoxy-4-[(3-fluorobenzyl)oxy]aniline (2.67 g, 10.8 mmol) to give the title compound as a white solid (2.06 g, 54%); NMR Spectrum: 3.79 (t, 2H), 3.80 (s, 3H), 4.31 (t, 2H), 5.12 (s, 2H), 7.03 (d, 1H), 7.18 (m, 2H), 7.29 (m, 2H), 7.35 (d, 1H), 7.45 (q, 1H), 8.22 (s, 1H); Mass Spectrum: 426 (MH+).

Sources & evidence

ORD record
ord-f55400ea7c46483db0355d7fd3edcbe9
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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