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

HRID 1867687Notes

Reaction equation

HRID 1867687 reaction equation
[Cl:1][C:2]1[C:3]([F:33])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:31][CH3:32])=[C:16]([CH2:19][N:20]([CH3:30])[C:21]4([C:27]([OH:29])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:34]=O>>[Cl:1][C:2]1[C:3]([F:33])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:31][CH3:32])=[C:16]([CH2:19][N:20]([CH3:30])[C:21]4([C:27]([OH:29])=[O:28])[CH2:26][CH2:25][N:24]([CH3:34])[CH2:23][CH2:22]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 690481224-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid

Product 1

HCID 579798044-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-methylpiperidine-4-carboxylic acid

Procedure

4-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid was reacted with para-formaldehyde using an analogous method to that described for the equivalent step in Example 11 to give 4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-methylpiperidine-4-carboxylic acid; 1H NMR Spectrum: (DMSO-d6+CD3COOD) 2.04 (m, 2H); 2.17 (m, 2H); 2.27 (s, 3H); 2.45-2.55 (m, 3H+ DMSO); 2.68 (m, 2H); 3.06 (m, 2H); 3.72 (s, 2H); 3.95 (s, 3H); 7.20 (s, 1H); 7.28 (t, 1H); 7.48 (t, 1H); 7.57 (t, 1H); 8.32 (s, 1H); 8.42 (s, 1H); Mass Spectrum: (M+H)+ 488.

Sources & evidence

ORD record
ord-46553f4f0ef74e73b70a333c80b6d75a
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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