Formaldehyde → 3-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]-1-methylazetidine-3-carboxamide

HRID 1867743Notes

Reaction equation

HRID 1867743 reaction equation
Cl.[Cl:2][C:3]1[C:4]([F:33])=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:31][CH3:32])=[C:17]([CH2:20][N:21]([CH2:29][CH3:30])[C:22]4([C:26]([NH2:28])=[O:27])[CH2:25][NH:24][CH2:23]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:34]=O>>[Cl:2][C:3]1[C:4]([F:33])=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:31][CH3:32])=[C:17]([CH2:20][N:21]([CH2:29][CH3:30])[C:22]4([C:26]([NH2:28])=[O:27])[CH2:25][N:24]([CH3:34])[CH2:23]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 690472513-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]azetidine-3-carboxamide hydrochloride salt

Product 1

HCID 579798813-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]-1-methylazetidine-3-carboxamideYield 55%

Procedure

3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]azetidine-3-carboxamide hydrochloride salt (Example 75) was coupled with aqueous formaldehyde using the same method as for the equivalent step in Example 76 to give 3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]-1-methylazetidine-3-carboxamide (55%) as a white powder; 1H NMR Spectrum: (CDCl3) 1.03 (t, 3H), 2.45 (s, 3H), 2.83 (q, 2H), 3.37 (brs, 2H), 3.65 (m, 2H), 3.97 (s, 3H), 4.05 (s, 2H), 5.41 (brs, 1H), 7.16 (m, 2H), 7.22 (s, 1H), 7.47 (brs, 1H), 7.95 (brs, 1H), 8.28 (s, 1H), 8.59 (m, 1H), 8.76 (s, 1H); Mass Spectrum: (M+H)+ 473.

Sources & evidence

ORD record
ord-af79fc9dfa03460abec3488d365135f6
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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