3-Methyl-4-(pyridin-2-ylmethoxy)aniline → 2-[(4-{[3-methyl-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethanol

HRID 550416

Reaction equation

HRID 550416 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][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)N>>[CH3:17][C:18]1[CH:19]=[C:20]([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:22]=[CH:23][C:24]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

3

Reactant 2

HCID 234382883-Methyl-4-(pyridin-2-ylmethoxy)anilineHCID 67020529N'-[4-cyano-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-N,N-dimethylimidoformamide

Product 1

HCID 115963042-[(4-{[3-methyl-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethanolYield 90%

Procedure

The procedure described in Example 1 was repeated using N′-[4-cyano-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-N,N-dimethylimidoformamide (200 mg, 0.9 mmol) and 3-methyl-4-(pyridin-2-ylmethoxy)aniline (231 mg, 1.08 mmol) to give the title compound as a white solid (317 mg, 90%); NMR Spectrum: 2.27 (s, 3H), 3.79 (s, 2H), 4.30 (t, 2H), 5.20 (s, 2H), 7.01 (d, 1H), 7.35 (dd, 1H), 7.40 (s+d, 2H), 7.74 (d, 1H), 7.84 (t, 1H), 8.21 (s, 1H), 8.33 (s, 1H), 8.59 (d, 1H); Mass Spectrum: 393 (MH+).

Sources & evidence

ORD record
ord-c857e960a02b45998b556207085a014c
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Linked notes

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