Glycolic Acid → N-[2-({4-[3-Chloro-4-hydroxyanilino]quinazolin-5-yl}oxy)ethyl]-2-hydroxy-N-methylacetamide

HRID 1864197Notes

Reaction equation

HRID 1864197 reaction equation
[Cl: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:29])(=O)[CH2:26][OH:27]>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[OH:24])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[O:19][CH2:20][CH2:21][N:22]([CH3:23])[C:25](=[O:29])[CH2:26][OH:27])[N:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 690575902-Chloro-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol

Product 1

HCID 69055535N-[2-({4-[3-Chloro-4-hydroxyanilino]quinazolin-5-yl}oxy)ethyl]-2-hydroxy-N-methylacetamideYield 58%

Procedure

2-Chloro-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol was reacted with glycolic acid using an analogous procedure to that described in Example 3 to give N-[2-({4-[3-Chloro-4-hydroxyanilino]quinazolin-5-yl}oxy)ethyl]-2-hydroxy-N-methylacetamide in 58% yield; NMR spectrum (DMSO-d6) 2.96 (s, 3H), 3.90 (t, 2H), 4.05 (m, 3H), 4.41 (t, 2H), 6.97 (d, 1H), 7.14 (d, 1H), 7.34 (m, 2H), 7.70 (t, 1H), 7.79 (d, 1H), 8.40 (s, 1H), 9.64 (s, 1H), 10.00 (bs, 1H); Mass spectrum MH+ 403.

Sources & evidence

ORD record
ord-bca12de28e3846fa9f37491edddab30a
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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