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

HRID 1867691Notes

Reaction equation

HRID 1867691 reaction equation
[Cl:1][C:2]1[C:3]([F:23])=[C:4]([CH:20]=[CH:21][CH:22]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:16]=O)[CH:14]=2)[N:9]=[CH:8][N:7]=1.[NH2:24][C:25]1([C:31]([OH:33])=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[Cl:1][C:2]1[C:3]([F:23])=[C:4]([NH:5][C:6]2[C:15]3[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH2:16][NH:24][C:25]4([C:31]([OH:33])=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:14]=3)[N:9]=[CH:8][N:7]=2)[CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 27344014-aminotetrahydro-2H-pyran-4-carboxylic acidHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 579798634-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]tetrahydro-2H-pyran-4-carboxylic acid

Procedure

4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with 4-aminotetrahydro-2H-pyran-4-carboxylic acid using an analogous method to that described for the equivalent step in Example 1 to give 4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]tetrahydro-2H-pyran-4-carboxylic acid; 1H NMR Spectrum: (DMSO-d6) 1.62-1.74 (m, 2H), 1.92-2.03 (m, 2H), 3.46-3.56 (m, 2H), 3.76 (s, 2H), 3.76-3.85 (m, 2H), 3.94 (s, 3H), 7.18 (s, 1H), 7.23-7.31 (m, 1H), 7.43-7.57 (m, 2H), 8.38 (s, 1H), 8.42 (s, 1H), 9.81 (brs, 1H). Mass Spectrum: (M+H)+ 461.

Sources & evidence

ORD record
ord-a1d15e1b4e1a48b7b83ae76d19c88927
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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