Acetaldehyde → 1-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]cyclopropanecarboxylic acid

HRID 1867749Notes

Reaction equation

HRID 1867749 reaction equation
[Cl:1][C:2]1[C:3]([F:29])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:27][CH3:28])=[C:16]([CH2:19][NH:20][C:21]4([C:24]([OH:26])=[O:25])[CH2:23][CH2:22]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH:30](=O)[CH3:31]>>[Cl:1][C:2]1[C:3]([F:29])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:27][CH3:28])=[C:16]([CH2:19][N:20]([CH2:30][CH3:31])[C:21]4([C:24]([OH:26])=[O:25])[CH2:23][CH2:22]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 177AcetaldehydeHCID 69047414HCID 69047414, compound

Product 1

HCID 579798081-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]cyclopropanecarboxylic acid

Procedure

1-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]cyclopropanecarboxylic acid (prepared as described in Example 27) was reacted with acetaldehyde using an analogous method to that described for the equivalent step in Example 24 to give 1-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]cyclopropanecarboxylic acid; 1H NMR Spectrum: (DMSO d6) 0.90 (t, 3H); 0.95-1.30 (m, 4H); 2.90 (m, 2H); 3.91 (s, 3H); 4.08 (s, 2H); 7.12 (s, 1H); 7.28 (dd, 1H); 7.40-7.60 (m, 2H); 8.20 (s, 1H); 8.40 (s, 1H); 9.65 (bs, 1H), 12.18 (bs, 1H); Mass Spectrum: (M+H)+ 445.

Sources & evidence

ORD record
ord-25a19d68c78f47e09c728b01113c1317
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

Loading…