N,N-Dimethylglycine → N1-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N2,N2-dimethylglycinamide

HRID 1864241Notes

Reaction equation

HRID 1864241 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[C:14]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[C:25]([Cl:37])[CH:24]=1)=[N:15][CH:16]=[N:17]2>>[Cl:37][C:25]1[CH:24]=[C:23]([NH:22][C:14]2[C:13]3[C:18](=[CH:19][CH:20]=[CH:21][C:12]=3[O:11][CH2:10][CH2:9][NH:8][C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[N:17]=[CH:16][N:15]=2)[CH:28]=[CH:27][C:26]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1

Participants

3

Reactant 2

HCID 673N,N-DimethylglycineHCID 690577145-(2-aminoethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine

Product 1

HCID 57974364N1-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N2,N2-dimethylglycinamideYield 31%

Procedure

The procedure described in Example 1 was repeated using N,N-dimethylglycine 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 31% yield; NMR spectrum (DMSO-d6) 2.08 (s, 6H), 2.79 (s, 2H), 3.68 (q, 2H), 4.36 (t, 2H), 5.29 (s, 2H), 7.13 (d, 1H), 7.21 (d, 1H), 7.34 (m, 2H), 7.55 (m, 2H), 7.70 (t, 1H), 7.86 (dt, 1H), 7.98 (d, 1H), 8.11 (t, 1H), 8.45 (s, 1H), 8.58 (d, 1H), 9.80 (s, 1H); Mass Spectrum MH+ 507.

Sources & evidence

ORD record
ord-bdb8837033364b9badcaf6a0c83e5ebf
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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