Formaldehyde → 4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]tetrahydro-2H-pyran-4-carboxylic acid

HRID 1867693Notes

Reaction equation

HRID 1867693 reaction equation
[Cl:1][C:2]1[C:3]([F:32])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:30][CH3:31])=[C:16]([CH2:19][NH:20][C:21]4([C:27]([OH:29])=[O:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:33]=O>>[Cl:1][C:2]1[C:3]([F:32])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:30][CH3:31])=[C:16]([CH2:19][N:20]([CH3:33])[C:21]4([C:27]([OH:29])=[O:28])[CH2:26][CH2:25][O:24][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 579798634-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]tetrahydro-2H-pyran-4-carboxylic acid

Product 1

HCID 579798244-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]tetrahydro-2H-pyran-4-carboxylic acid

Procedure

4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]tetrahydro-2H-pyran-4-carboxylic acid was coupled 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]tetrahydro-2H-pyran-4-carboxylic acid; 1H NMR Spectrum: (DMSO-d6) 1.70-1.89 (m, 2H), 2.05-2.19 (m, 2H), 2.20 (s, 3H), 3.10-3.60 (m, 2H+ H2O), 3.70 (s, 2H), 3.88 (m, 2H), 3.93 (s, 3H), 7.18 (s, 1H), 7.28 (m, 1H), 7.40-7.60 (m, 2H), 8.30 (s, 1H), 8.41 (s, 1H), 9.76 (brs, 1H). Mass Spectrum: (M+H)+ 475.

Sources & evidence

ORD record
ord-cc0ae357998b4174a40b6db8482e3c68
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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