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

HRID 1867715Notes

Reaction equation

HRID 1867715 reaction equation
[Cl:1][C:2]1[C:3]([F:26])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:24][CH3:25])=[C:16]([CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.CC[O:29][C:30]([C@H:32](OS(C(F)(F)F)(=O)=O)[CH3:33])=[O:31]>>[Cl:1][C:2]1[C:3]([F:26])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:24][CH3:25])=[C:16]([CH2:19][N:20]([CH:21]([CH3:23])[CH3:22])[C@H:32]([C:30]([OH:29])=[O:31])[CH3:33])[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 69047474N-(3-chloro-2-fluorophenyl)-6-[(isopropylamino)methyl]-7-methoxyquinazolin-4-amine

Product 1

HCID 57979815N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-isopropyl-L-alanine

Procedure

N-(3-Chloro-2-fluorophenyl)-6-[(isopropylamino)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-isopropyl-L-alanine; 1H NMR Spectrum: (DMSO-d6) 1.08 (d, 6H); 1.31 (d, 3H); 3.10 (m, 1H); 3.63 (q, 1H); 3.98 (s, 3H); 4.02 (s, 2H); 7.20 (s, 1H); 7.29 (t, 1H); 7.49 (m, 1H); 7.59 (m, 1H); 8.42 (s, 2H); 9.68 (brs, 1H); Mass Spectrum: (M+H)+ 447.

Sources & evidence

ORD record
ord-4c3d48236f79485695af8b3030d55897
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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