2-Methanesulfonylacetic acid → N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-2-(methylsulfonyl)acetamide

HRID 1864243Notes

Reaction equation

HRID 1864243 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([OH:8])=O)(=[O:4])=[O:3].[NH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[C:26]([Cl:38])[CH:25]=1)=[N:16][CH:17]=[N:18]2>>[Cl:38][C:26]1[CH:25]=[C:24]([NH:23][C:15]2[C:14]3[C:19](=[CH:20][CH:21]=[CH:22][C:13]=3[O:12][CH2:11][CH2:10][NH:9][C:6](=[O:8])[CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[N:18]=[CH:17][N:16]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1

Participants

3

Reactant 2

HCID 37328412-Methanesulfonylacetic acidHCID 690577145-(2-aminoethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine

Product 1

HCID 11421373N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-2-(methylsulfonyl)acetamideYield 51%

Procedure

The procedure described in Example 1 was repeated using methanesulfonylacetic acid and 5-(2-aminoethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine (obtained as described in Example 2.6, preparation of starting materials) to give the title compound in 51% yield; NMR spectrum (DMSO-d6) 2.99 (s, 3H), 3.74 (m, 2H), 4.04 (s, 2H), 4.34 (t, 2H), 5.29 (s, 2H), 7.13 (d, 1H), 7.22 (d, 1H), 7.35 (m, 2H), 7.55 (m, 2H), 7.71 (t, 1H), 7.87 (dt, 1H), 8.03 (d, 1H), 8.46 (s, 1H), 8.58 (d, 1H), 8.76 (t, 1H), 9.79 (s, 1H); Mass Spectrum MH+ 542.

Sources & evidence

ORD record
ord-df201b8df41347ab8648b9e9dc0ee75b
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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