N,N-Dimethylethylenediamine → N'-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N,N-dimethylethane-1,2-diamine

HRID 1867704Notes

Reaction equation

HRID 1867704 reaction equation
[Cl:1][C:2]1[C:3]([F:23])=[C:4]([CH:20]=[CH:21][CH:22]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:16]=O)[CH:14]=2)[N:9]=[CH:8][N:7]=1.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][NH2:28]>>[Cl:1][C:2]1[C:3]([F:23])=[C:4]([NH:5][C:6]2[C:15]3[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH2:16][NH:28][CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])[CH:14]=3)[N:9]=[CH:8][N:7]=2)[CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 69048232N'-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N,N-dimethylethane-1,2-diamine

Procedure

4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with N,N-dimethylethane-1,2-diamine using an analogous method to that described for the equivalent step in Example 1 to give N′-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N,N-dimethylethane-1,2-diamine; 1H NMR Spectrum: (DMSO-d6) 2.12 (s, 6H); 2.37 (t, 2H); 2.65 (t, 2H); 3.85 (s, 2H); 3.97 (s, 3H); 7.21 (s, 1H); 7.28 (t, 1H); 7.51 (m, 2H); 8.32 (s, 1H); 8.43 (s, 1H); 9.78 (s, 1H); Mass Spectrum: (M+H)+ 404.

Sources & evidence

ORD record
ord-0114e4d0468f4276b9252eddfc105d32
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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