Acetic Acid → N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide

HRID 1864290Notes

Reaction equation

HRID 1864290 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:19][CH2:20][CH2:21][NH:22][CH3:23])[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[OH:24].[C:25]([OH:28])(=O)[CH3:26]>>[OH:24][C:3]1[CH:4]=[CH:5][C:6]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:19][CH2:20][CH2:21][N:22]([CH3:23])[C:25](=[O:28])[CH3:26])[N:12]=[CH:11][N:10]=2)=[CH:7][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 690540072-Methyl-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol

Product 1

HCID 69059574N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamideYield 100%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using acetic acid and 2-methyl-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol (obtained as described in Example 3, preparation of starting materials) to give N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide as a light brown solid in 100% yield; NMR spectrum (DMSO-d6) 1.90 (s, 3H), 2.16 (s, 3H), 3.02 (s, 3H), 3.85 (t, 2H), 4.45 (t, 2H), 6.82 (d, 1H), 7.18 (dd, 1H), 7.25 (d, 1H), 7.34 (m, 2H), 7.92 (t, 1H), 8.65 (s, 1H), 9.45 (s, 1H), 10.52 (s, 1H); Mass spectrum MH+ 367.

Workup

  1. customThe procedure described in Example 3 (preparation of starting materials)

Sources & evidence

ORD record
ord-f2ddc091239f451487e8cdff49e5be01
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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