4-(Chloromethyl)-1,3-thiazole → N-Methyl-N-{2-[(4-{[3-methyl-4-(1,3-thiazol-4-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}acetamide

HRID 1864291Notes

Reaction equation

HRID 1864291 reaction equation
Cl[CH2:2][C:3]1[N:4]=[CH:5][S:6][CH:7]=1.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[O:26][CH2:27][CH2:28][N:29]([CH3:33])[C:30](=[O:32])[CH3:31])[N:19]=[CH:18][N:17]=2)=[CH:11][C:10]=1[CH3:34]>>[CH3:33][N:29]([CH2:28][CH2:27][O:26][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:25]=1[C:16]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:2][C:3]3[N:4]=[CH:5][S:6][CH:7]=3)=[C:10]([CH3:34])[CH:11]=1)=[N:17][CH:18]=[N:19]2)[C:30](=[O:32])[CH3:31]

Participants

3

Reactant 2

HCID 27632904-(Chloromethyl)-1,3-thiazoleHCID 69059574N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide

Product 1

HCID 57974294N-Methyl-N-{2-[(4-{[3-methyl-4-(1,3-thiazol-4-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}acetamideYield 5%

Procedure

The procedure described in Example 3 was repeated using 4-(chloromethyl)-1,3-thiazole and N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide (obtained as described in Example 75, preparation of starting materials) to give the title compound as an off-white solid in 5% yield; NMR spectrum (DMSO-d6 373K) 1.94 (s, 3H), 2.24 (s, 3H), 2.99 (s, 3H), 3.87 (t, 2H), 4.46 (m, 2H), 5.25 (s, 2H), 7.08 (d, 1H), 7.17 (d, 1H), 7.35 (d, 1H), 7.47 (d, 1H), 7.54 (dd, 1H), 7.70 (m, 2H), 8.41 (s, 1H), 9.07 (d, 1H), 9.63 (s, 1H); Mass spectrum MH+ 464.

Sources & evidence

ORD record
ord-8f356fdcef804853b8cc9d7313c9bd51
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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