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

HRID 1864293Notes

Reaction equation

HRID 1864293 reaction equation
Cl[CH2:2][C:3]1[S:4][CH:5]=[CH:6][N:7]=1.[OH:8][CH2:9][C:10]([N:12]([CH2:14][CH2:15][O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[C:19]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH3:35])[CH:29]=1)=[N:20][CH:21]=[N:22]2)[CH3:13])=[O:11]>>[OH:8][CH2:9][C:10]([N:12]([CH3:13])[CH2:14][CH2:15][O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[C:19]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:2][C:3]3[S:4][CH:5]=[CH:6][N:7]=3)=[C:30]([CH3:35])[CH:29]=1)=[N:20][CH:21]=[N:22]2)=[O:11]

Participants

3

Reactant 2

HCID 140908642-(Chloromethyl)-1,3-thiazoleHCID 690579972-Hydroxy-N-[2-({4-[4-hydroxy-3-methylanilino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide

Product 1

HCID 113860592-Hydroxy-N-methyl-N-{2-[(4-{[3-methyl-4-(1,3-thiazol-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}acetamideYield 38%

Procedure

The procedure described in Example 3 was repeated using 2-(chloromethyl)-1,3-thiazole and 2-hydroxy-N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide (obtained as described in Example 3, preparation of starting materials) to give the title compound as a white solid in 38% yield; NMR spectrum (DMSO-d6 373K) 2.27 (s, 3H), 2.98 (s, 3H), 3.91 (t, 2H), 4.07 (s, 2H), 4.47 (t, 2H), 5.44 (s, 2H), 7.09 (d, 1H), 7.16 (d, 1H), 7.34 (d, 1H), 7.54 (m, 2H), 7.67 (t, 1H), 7.70 (d, 1H), 7.83 (d, 1H), 8.41 (s, 1H), 9.63 (s, 1H); Mass spectrum MH+ 480.

Sources & evidence

ORD record
ord-7e06948ae0664ad68c5b2cde25ab787f
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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