3-(Chloromethyl)-5-ethyl-1,2-oxazole → 2-Hydroxy-N-methyl-N-((2R)-2-{[4-({3-methyl-4-[(5-methylisoxazol-3-yl)methoxy]phenyl}amino)quinazolin-5-yl]oxy}propyl)acetamide

HRID 1864316Notes

Reaction equation

HRID 1864316 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[C:6]([CH2:8]C)[O:5][N:4]=1.[OH:10][CH2:11][C:12]([N:14]([CH2:16][C@H:17]([O:19][C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[C:22]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([CH3:38])[CH:32]=1)=[N:23][CH:24]=[N:25]2)[CH3:18])[CH3:15])=[O:13]>>[OH:10][CH2:11][C:12]([N:14]([CH3:15])[CH2:16][C@H:17]([O:19][C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[C:22]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:2][C:3]3[CH:7]=[C:6]([CH3:8])[O:5][N:4]=3)=[C:33]([CH3:38])[CH:32]=1)=[N:23][CH:24]=[N:25]2)[CH3:18])=[O:13]

Participants

3

Reactant 2

HCID 142672983-(Chloromethyl)-5-ethyl-1,2-oxazoleHCID 690577712-hydroxy-N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]-N-methylacetamide

Product 1

HCID 579743602-Hydroxy-N-methyl-N-((2R)-2-{[4-({3-methyl-4-[(5-methylisoxazol-3-yl)methoxy]phenyl}amino)quinazolin-5-yl]oxy}propyl)acetamideYield 7%

Procedure

The procedure described in Example 3 was repeated using 3-(chloromethyl)-5-ethylisoxazole and 2-hydroxy-N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]-N-methylacetamide (obtained as described in Example 90, preparation of starting materials) to give the title compound as a white solid in 7% yield; NMR spectrum (DMSO-d6 373K) 1.44 (d, 3H), 2.22 (s, 3H), 2.42 (s, 3H), 2.98 (s, 3H), 3.58 (m, 1H), 4.17 (m, 3H), 5.11 (m, 1H), 5.15 (s, 2H), 6.29 (s, 1H), 7.07 (d, 1H), 7.11 (d, 1H), 7.33 (d, 1H), 7.57 (m, 2H), 7.69 (t, 1H), 8.44 (s, 1H), 9.83 (s, 1H); Mass spectrum MH+ 492.

Sources & evidence

ORD record
ord-67533efdceae40c3990ca9e35c3c3a6b
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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