Formaldehyde → N2-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N2,2-dimethylalaninamide

HRID 1867766Notes

Reaction equation

HRID 1867766 reaction equation
[Cl:1][C:2]1[C:3]([F:29])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:27][CH3:28])=[C:16]([CH2:19][NH:20][C:21]([CH3:26])([C:23]([NH2:25])=[O:24])[CH3:22])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:30]=O>>[Cl:1][C:2]1[C:3]([F:29])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:27][CH3:28])=[C:16]([CH2:19][N:20]([CH3:30])[C:21]([CH3:26])([C:23]([NH2:25])=[O:24])[CH3:22])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 57979860N2-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-2-methylalaninamide

Product 1

HCID 57979805N2-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N2,2-dimethylalaninamideYield 76%

Procedure

N2-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-2-methylalaninamide (Example 97) was coupled with aqueous formaldehyde using an analogous method to that described for the equivalent step in Example 96 to give the title product as a white solid, (0.078 g, 76%); 1H NMR Spectrum: (DMSO-d6) 1.24 (s, 3H), 2.14 (s, 3H), 3.55 (s, 2H), 3.95 (s, 3H), 7.11 (m, 1H), 7.21 (s, 1H), 7.30 (t, 1H), 7.37 (m, 1H), 7.52-7.58 (m, 2H), 8.44 (m, 2H), 9.76 (s, 1H); Mass Spectrum: (M+H)+ 432.

Sources & evidence

ORD record
ord-10062398cb1840b4b877069f62858d3e
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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