1-Aminocyclopent-3-ene-1-carboxylic acid → HCID 69048166, compound

HRID 1867696Notes

Reaction equation

HRID 1867696 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.[NH2:24][C:25]1([C:30]([OH:32])=[O:31])[CH2:29][CH:28]=[CH:27][CH2:26]1>>[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][NH:24][C:25]4([C:30]([OH:32])=[O:31])[CH2:29][CH:28]=[CH:27][CH2:26]4)[CH:14]=3)[N:9]=[CH:8][N:7]=2)[CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 109535161-Aminocyclopent-3-ene-1-carboxylic acidHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 69048166HCID 69048166, compound

Procedure

4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with 1-aminocyclopent-3-ene carboxylic acid using an analogous method to that described for the equivalent step in Example 1 to give 1-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]cyclopent-3-ene-1-carboxylic acid; 1H NMR Spectrum: (DMSO-d6) 2.63 (d, 2H); 2.93 (d, 2H); 3.91 (s, 2H); 3.97 (s, 3H); 5.68 (s, 2H); 7.21 (s, 1H); 7.27 (t, 1H); 7.50 (m, 2H); 8.45 (s, 1H); 8.50 (s, 1H); 10.09 (s, 1H); Mass Spectrum: (M+H)+ 443.

Sources & evidence

ORD record
ord-4a32da8f67b24e2fbb96aee4eadee6aa
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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