Formaldehyde → 4-(((4-(3-Chloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yl)methyl)(methyl)amino)-1-methylpiperidine-4-carboxamide

HRID 1867682Notes

Reaction equation

HRID 1867682 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]([NH2:29])=[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]([NH2:29])=[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 57979867HCID 57979867, compound

Product 1

HCID 116200554-(((4-(3-Chloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yl)methyl)(methyl)amino)-1-methylpiperidine-4-carboxamide

Procedure

4-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxamide (Example 16) was reacted with paraformaldehyde 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-carboxamide; 1H NMR Spectrum: (DMSO d6) 1.80 (m, 2H); 2.03-2.17 (m, 10H); 2.66 (m, 2H); 3.64 (s, 2H); 3.95 (s, 3H); 7.08 (s, 1H); 7.17 (m, 2H); 7.30 (t, 1H); 7.51 (m, 1H); 7.57 (m, 1H); 8.34 (s, 1H); 8.42 (s, 1H); 9.68 (s, 1H). Mass Spectrum: (M+H)+ 487.

Sources & evidence

ORD record
ord-6eec435b1e2f48b494ccbd405c56b260
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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