3-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)aniline → N-{2-[(4-{[3-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N-methylacetamide

HRID 1864358Notes

Reaction equation

HRID 1864358 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][CH2:14][N:15]([CH3:19])[C:16](=[O:18])[CH3:17])[N:5]=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[O:28][C:29]([CH3:37])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[CH3:30])[NH2:24]>>[Cl:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[O:12][CH2:13][CH2:14][N:15]([CH3:19])[C:16](=[O:18])[CH3:17])[N:5]=[CH:4][N:3]=2)[CH:25]=[CH:26][C:27]=1[O:28][C:29]([CH3:30])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[CH3:37]

Participants

3

Reactant 2

HCID 690590593-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)anilineHCID 86615689N-{2-[(4-Chloroquinazolin-5-yl)oxy]ethyl}-N-methylacetamide

Product 1

HCID 57974354N-{2-[(4-{[3-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N-methylacetamideYield 31%

Procedure

The procedure described in Example 126 was repeated using N-{2-[(4-chloroquinazolin-5-yl)oxy]ethyl}-N-methylacetamide (obtained as described in Example 126, preparation of starting materials, 47 mg, 0.170 mmol) and 3-chloro-4-(1-methyl-1-pyridin-2-ylethoxy)aniline (49 mg, 0.187 mmol) to give the title compound in 31% yield; NMR Spectrum (DMSO-d6, 400 MHz, 373K) 1.75 (s, 6H), 1.92 (s, 3H), 2.94 (s, 3H), 3.88 (t, 2H), 4.47 (t, 2H), 6.62 (d, 1H), 7.16 (d, 1H), 7.31 (ddd, 1H), 7.35 (d, 1H), 7.39 (dd, 1H), 7.70 (dd, 1H), 7.75 (dd, 1H), 7.83 (ddd, 1H), 7.99 (d, 1H), 8.46 (s, 1H), 8.58 (dd, 1H), 9.70 (s, 1H); Mass spectrum MH+ 506.0.

Sources & evidence

ORD record
ord-b6fc1b8c00244cdb87466758e460f02b
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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