Picolyl chloride → N-Methyl-N-{2-[(4-{[3-methyl-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}acetamide

HRID 1864289Notes

Reaction equation

HRID 1864289 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[O:27][CH2:28][CH2:29][N:30]([CH3:34])[C:31](=[O:33])[CH3:32])[N:20]=[CH:19][N:18]=2)=[CH:12][C:11]=1[CH3:35]>>[CH3:34][N:30]([CH2:29][CH2:28][O:27][C:25]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:26]=1[C:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=3)=[C:11]([CH3:35])[CH:12]=1)=[N:18][CH:19]=[N:20]2)[C:31](=[O:33])[CH3:32]

Participants

3

Reactant 2

HCID 23393Picolyl chlorideHCID 69059574N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide

Product 1

HCID 11419727N-Methyl-N-{2-[(4-{[3-methyl-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}acetamideYield 11%

Procedure

The procedure described in Example 3 was repeated using 2-(chloromethyl)pyridine and N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide to give the title compound as a white solid in 11% yield; NMR spectrum (DMSO-d6 373K) 1.94 (s, 3H), 2.28 (s, 3H), 3.00 (s, 3H), 3.88 (t, 2H), 4.46 (m, 2H), 5.20 (s, 2H), 7.01 (d, 1H), 7.16 (d, 1H), 7.34 (m, 2H), 7.51 (m, 2H), 7.55 (d, 1H), 7.68 (t, 1H), 7.83 (td, 1H), 8.41 (s, 1H), 8.58 (d, 1H), 9.63 (s, 1H); Mass spectrum MH+ 458.

Sources & evidence

ORD record
ord-c56b0de97e7744d7aa4617aa2f29619c
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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