Ethylamine → N-(3-chloro-2-fluorophenyl)-6-[(ethylamino)methyl]-7-methoxyquinazolin-4-amine

HRID 1867712Notes

Reaction equation

HRID 1867712 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.[CH2:24]([NH2:26])[CH3:25]>>[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:26][CH2:24][CH3:25])[CH:14]=3)[N:9]=[CH:8][N:7]=2)[CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 6341EthylamineHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 69046738N-(3-chloro-2-fluorophenyl)-6-[(ethylamino)methyl]-7-methoxyquinazolin-4-amine

Procedure

4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with ethylamine using an analogous method to that described for the equivalent step in Example 1 to give N-(3-chloro-2-fluorophenyl)-6-[(ethylamino)methyl]-7-methoxyquinazolin-4-amine; 1H NMR Spectrum: (DMSO-d6) 1.09 (t, 3H); 2.63 (q, 2H); 3.83 (s, 2H); 3.97 (s, 3H); 7.20 (s, 1H); 7.27 (t, 1H); 7.50 (m, 2H); 8.33 (s, 1H); 8.43 (s, 1H); 9.77 (s, 1H); Mass Spectrum: (M+H)+ 361.

Sources & evidence

ORD record
ord-7d730cfac40a4868a38d1701b85e7e7d
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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