2-Methoxyethylamine → N-(3-chloro-2-fluorophenyl)-7-methoxy-6-{[(2-methoxyethyl)amino]methyl}quinazolin-4-amine

HRID 1867706Notes

Reaction equation

HRID 1867706 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.[NH2:24][CH2:25][CH2:26][O:27][CH3:28]>>[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:24][CH2:25][CH2:26][O:27][CH3:28])[CH:14]=3)[N:9]=[CH:8][N:7]=2)[CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 69047438N-(3-chloro-2-fluorophenyl)-7-methoxy-6-{[(2-methoxyethyl)amino]methyl}quinazolin-4-amine

Procedure

4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with aminoethylmethyl ether using an analogous method to that described for the equivalent step in Example 1 to give N-(3-chloro-2-fluorophenyl)-7-methoxy-6-{[(2-methoxyethyl)amino]methyl}quinazolin-4-amine; 1H NMR Spectrum: (DMSO-d6) 2.15 (brs, 1H); 2.76 (t, 2H); 3.25 (s, 3H); 3.46 (t, 2H); 3.85 (s, 2H); 3.97 (s, 3H); 7.21 (s, 1H); 7.28 (t, 1H); 7.51 (m, 2H); 8.33 (s, 1H); 8.44 (s, 1H); 9.78 (s, 1H); Mass Spectrum: (M+H)+ 391.

Sources & evidence

ORD record
ord-6c11a269a1d3475e84a4dc59184e94bf
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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