4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde → HCID 11691173, compound

HRID 1867676Notes

Reaction equation

HRID 1867676 reaction equation
[Cl:1][C:2]1[C:3]([F:23])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH:19]=O)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:24][NH:25][C@H:26]([C:31]([NH2:33])=[O:32])[CH2:27][CH2:28][O:29][CH3:30]>>[Cl:1][C:2]1[C:3]([F:23])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH2:19][N:25]([CH3:24])[C@H:26]([C:31]([NH2:33])=[O:32])[CH2:27][CH2:28][O:29][CH3:30])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehydeHCID 55283965HCID 55283965, compound

Product 1

HCID 11691173HCID 11691173, compound

Procedure

4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde was coupled with N2,O-dimethyl-L-homoserinamide analogously as for the equivalent step in Example 1 to give N2-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N2,O-dimethyl-L-homoserinamide; 1H NMR spectrum: (DMSO d6) 1.91 (m, 2H), 2.25 (s, 3H), 3.23 (s, 3H), 3.27 (t, 1H), 3.39 (m, 1H), 3.48 (m, 1H), 3.66 (d, 1H), 3.81 (d, 1H), 3.96 (s, 3H), 7.07 (brs, 1H), 7.20 (s, 1H), 7.29 (t, 1H), 7.38 (brs, 1H), 7.49 (t, 1H), 7.55 (t, 1H), 8.35 (s, 1H), 8.43 (s, 1H), 9.77 (s, 1H); Mass Spectrum: (M+H)+ 462.

Sources & evidence

ORD record
ord-d6354d209442494dbeceae31d1a8e9e8
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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