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

HRID 1864314Notes

Reaction equation

HRID 1864314 reaction equation
[C:1]([OH:5])(=O)[CH2:2][OH:3].[CH3:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[O:24][C@H:25]([CH3:29])[CH2:26][NH:27][CH3:28])[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:9][C:8]=1[OH:30]>>[OH:3][CH2:2][C:1]([N:27]([CH2:26][C@H:25]([O:24][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:23]=1[C:14]([NH:13][C:11]1[CH:10]=[CH:9][C:8]([OH:30])=[C:7]([CH3:6])[CH:12]=1)=[N:15][CH:16]=[N:17]2)[CH3:29])[CH3:28])=[O:5]

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 690595682-methyl-4-({5-[(1R)-1-methyl-2-(methylamino) ethoxy]quinazolin-4-yl}amino)phenol

Product 1

HCID 690577712-hydroxy-N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]-N-methylacetamideYield 81%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using glycolic acid and 2-methyl-4-({5-[(1R)-1-methyl-2-(methylamino) ethoxy]quinazolin-4-yl}amino)phenol to give 2-hydroxy-N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]-N-methylacetamide as an orange solid in 81% yield; NMR spectrum (DMSO-d6) 1.38 (d, 3H), 2.15 (s, 3H), 2.96 (s, 3H), 3.35 (dd, 1H), 4.02 (s, 2H), 4.21 (m, 2H), 5.18 (m, 1H), 6.83 (d, 1H), 7.27 (m, 1H), 7.38 (s, 1H), 7.46 (d, 1H), 7.92 (t, 1H), 8.70 (s, 1H), 9.52 (s, 1H), 10.68 (s, 1H); Mass spectrum MH+ 397.

Workup

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

Sources & evidence

ORD record
ord-9e8e6d3822934ea5940bcb98fead8cea
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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