3-Hydroxy-2,2-dimethylpropionic acid → N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-3-hydroxy-N,2,2-trimethylpropanamide

HRID 1864232Notes

Reaction equation

HRID 1864232 reaction equation
[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=O.[Cl:9][C:10]1[CH:11]=[C:12]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][C:33]=3[O:35][CH2:36][CH2:37][NH:38][CH3:39])[N:28]=[CH:27][N:26]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>>[Cl:9][C:10]1[CH:11]=[C:12]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][C:33]=3[O:35][CH2:36][CH2:37][N:38]([CH3:39])[C:4](=[O:6])[C:3]([CH3:8])([CH3:7])[CH2:2][OH:1])[N:28]=[CH:27][N:26]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

3

Reactant 2

HCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 69065361N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine

Product 1

HCID 57974292N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-3-hydroxy-N,2,2-trimethylpropanamideYield 25%

Procedure

The procedure described in Example 1 was repeated using 3-hydroxy-2,2-dimethylpropanoic acid and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine (obtained as described in Example 1, preparation of starting materials) to give the title compound in 25% yield; NMR spectrum (DMSO-d6) 1.07 (s, 6H), 3.15 (s, 3H), 3.35 (d, 2H), 3.91 (t, 2H), 4.41-4.48 (m, 3H), 5.30 (s, 2H), 7.18 (d, 1H), 7.24 (d, 1H), 7.34 (d, 1H), 7.35-7.39 (m, 1H), 7.56-7.61 (m, 2H), 7.71-7.76 (m, 1H), 7.86-7.91 (m, 1H), 7.98 (d, 1H), 8.45 (s, 1H), 8.60 (d, 1H), 9.81 (s, 1H); Mass spectrum MH+ 536.

Sources & evidence

ORD record
ord-d6e971eef6974e9096ace99e1659d286
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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