Formaldehyde → 1-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]cyclopent-3-ene-1-carboxylic acid

HRID 1867697Notes

Reaction equation

HRID 1867697 reaction equation
[Cl:1][C:2]1[C:3]([F:31])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:29][CH3:30])=[C:16]([CH2:19][NH:20][C:21]4([C:26]([OH:28])=[O:27])[CH2:25][CH:24]=[CH:23][CH2:22]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:32]=O>>[Cl:1][C:2]1[C:3]([F:31])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:29][CH3:30])=[C:16]([CH2:19][N:20]([CH3:32])[C:21]4([C:26]([OH:28])=[O:27])[CH2:22][CH:23]=[CH:24][CH2:25]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 69048166HCID 69048166, compound

Product 1

HCID 579798641-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]cyclopent-3-ene-1-carboxylic acid

Procedure

1-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]cyclopent-3-ene-1-carboxylic acid was methylated by reaction with paraformaldehyde using an analogous method to that described for the equivalent step in Example 11 to give 1-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]cyclopent-3-ene-1-carboxylic acid; 1H NMR Spectrum: (DMSO-d6) 2.21 (s, 3H); 2.62 (d, 2H); 2.99 (d, 2H); 3.73 (s, 2H); 3.95 (s, 3H); 5.71 (s, 2H); 7.20 (s, 1H); 7.29 (t, 1H); 7.52 (m, 2H); 8.34 (s, 1H); 8.42 (s, 1H); 9.77 (s, 1H); Mass Spectrum: (M+H)+ 457.

Sources & evidence

ORD record
ord-bc4216cbf4a1426081e0021427a1d6be
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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