Ethyl (R)-2-(trifluoromethylsulfonyloxy)propionate → n-({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-n-ethyl-l-alanine

HRID 1867713Notes

Reaction equation

HRID 1867713 reaction equation
[Cl:1][C:2]1[C:3]([F:25])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:23][CH3:24])=[C:16]([CH2:19][NH:20][CH2:21][CH3:22])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.CC[O:28][C:29]([C@H:31](OS(C(F)(F)F)(=O)=O)[CH3:32])=[O:30]>>[Cl:1][C:2]1[C:3]([F:25])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:23][CH3:24])=[C:16]([CH2:19][N:20]([CH2:21][CH3:22])[C@H:31]([C:29]([OH:28])=[O:30])[CH3:32])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10999437Ethyl (R)-2-(trifluoromethylsulfonyloxy)propionateHCID 69046738N-(3-chloro-2-fluorophenyl)-6-[(ethylamino)methyl]-7-methoxyquinazolin-4-amine

Product 1

HCID 57979809n-({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-n-ethyl-l-alanine

Procedure

N-(3-Chloro-2-fluorophenyl)-6-[(ethylamino)methyl]-7-methoxyquinazolin-4-amine was coupled with ethyl O-trifluoromethanesulfonyl-D-lactate and hydrolysed using analogous methods to those described for the equivalent steps in Example 46 to give N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-ethyl-L-alanine; 1H NMR Spectrum: (DMSO-d6) 1.03 (t, 3H); 1.29 (d, 3H); 2.71 (q, 2H); 3.56 (q, 1H); 3.86 (d, 1H); 3.94 (m, 4H); 7.19 (s, 1H); 7.28 (t, 1H); 7.48 (m, 1H); 7.56 (m, 1H); 8.41 (m, 2H); 9.76 (brs, 1H); Mass Spectrum: (M+H)+ 433.

Sources & evidence

ORD record
ord-ef71ea6b45564e7a94306c67c5265766
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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