Ethyl (R)-2-(trifluoromethylsulfonyloxy)propionate → N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-[2-(dimethylamino)ethyl]-L-alanine

HRID 1867705Notes

Reaction equation

HRID 1867705 reaction equation
[Cl:1][C:2]1[C:3]([F:28])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:26][CH3:27])=[C:16]([CH2:19][NH:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.CC[O:31][C:32]([C@H:34](OS(C(F)(F)F)(=O)=O)[CH3:35])=[O:33]>>[Cl:1][C:2]1[C:3]([F:28])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:26][CH3:27])=[C:16]([CH2:19][N:20]([CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])[C@H:34]([C:32]([OH:33])=[O:31])[CH3:35])[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 69048232N'-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N,N-dimethylethane-1,2-diamine

Product 1

HCID 57979818N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-[2-(dimethylamino)ethyl]-L-alanine

Procedure

N′-({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N,N-dimethylethane-1,2-diamine 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-[2-(dimethylamino)ethyl]-L-alanine; 1H NMR Spectrum: (DMSO-d6) 1.24 (d, 3H); 2.36 (s, 6H); 2.63 (m, 2H); 2.77 (m, 1H); 2.86 (m, 1H); 3.41 (q, 1H); 3.80 (d, 1H); 3.89 (d, 1H); 3.96 (s, 3H); 7.21 (s, 1H); 7.29 (t, 1H); 7.49 (t, 1H); 7.60 (t, 1H); 8.36 (s, 1H); 8.44 (s, 1H); 9.71 (brs, 1H); Mass Spectrum: (M+H)+ 476.

Sources & evidence

ORD record
ord-b2232650ca9b4fa4a245de10a2ce415f
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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