Glycolic Acid → N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-2-hydroxyacetamide

HRID 1864240Notes

Reaction equation

HRID 1864240 reaction equation
[C:1]([OH:5])(=O)[CH2:2][OH:3].[NH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[C:12]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)=[C:23]([Cl:35])[CH:22]=1)=[N:13][CH:14]=[N:15]2>>[Cl:35][C:23]1[CH:22]=[C:21]([NH:20][C:12]2[C:11]3[C:16](=[CH:17][CH:18]=[CH:19][C:10]=3[O:9][CH2:8][CH2:7][NH:6][C:1](=[O:5])[CH2:2][OH:3])[N:15]=[CH:14][N:13]=2)[CH:26]=[CH:25][C:24]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 690577145-(2-aminoethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine

Product 1

HCID 11375036N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-2-hydroxyacetamideYield 60%

Procedure

The procedure described in Example 1 was repeated using glycolic acid and 5-(2-aminoethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine (obtained as described in Example 2.6, preparation of starting materials) to give the title compound in 60% yield; NMR spectrum (DMSO-d6) 3.71 (q, 2H), 3.78 (d, 2H), 4.36 (t, 2H), 5.28 (s, 2H), 5.49 (t, 1H), 7.13 (d, 1H), 7.21 (d, 1H), 7.32 (d, 1H), 7.35 (m, 1H), 7.56 (m, 2H), 7.71 (t, 1H), 7.87 (dt, 1H), 7.98 (d, 1H), 8.18 (t, 1H), 8.45 (s, 1H), 8.58 (d, 1H), 9.82 (s, 1H); Mass Spectrum MH+ 480.

Sources & evidence

ORD record
ord-7e72d210905449a384f87f00f98f38a1
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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