N-(2-cyanoethyl)glycine → N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-(2-cyanoethyl)glycine

HRID 1867698Notes

Reaction equation

HRID 1867698 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.[C:24]([CH2:26][CH2:27][NH:28][CH2:29][C:30]([OH:32])=[O:31])#[N:25]>>[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][N:28]([CH2:27][CH2:26][C:24]#[N:25])[CH2:29][C:30]([OH:32])=[O:31])[CH:14]=3)[N:9]=[CH:8][N:7]=2)[CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 76526N-(2-cyanoethyl)glycineHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 57979828N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-(2-cyanoethyl)glycine

Procedure

4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with N-(2-cyanoethyl)glycine using an analogous method to that described for the equivalent step in Example 1 to give N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-(2-cyanoethyl)glycine; 1H NMR Spectrum: (DMSO-d6) 2.70 (t, 2H); 3.04 (t, 2H); 3.40 (s, 2H); 3.95 (m, 5H); 7.20 (s, 1H); 7.27 (t, 1H); 7.48 (t, 1H); 7.55 (t, 1H); 8.36 (s, 1H); 8.44 (s, 1H); 9.69 (brs, 1H); Mass Spectrum: (M+H)+ 444.

Sources & evidence

ORD record
ord-e3259f6707554361bc4f6f2c9921364d
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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