N-(6-formyl-1-isoquinolinyl)benzamide → 3-(4-{[3-(1-Amino-6-isoquinolinyl)-acryloyl](methyl)amino]piperidin-1-yl)-3-oxo-propionic acid methyl ester
Reaction equation
C(C1C=C2C(=CC=1)C(NC(=O)C1C=CC=CC=1)=NC=C2)=O.C([NH:29][C:30]1[C:39]2[C:34](=[CH:35][C:36]([CH:40]=[CH:41][C:42]([OH:44])=O)=[CH:37][CH:38]=2)[CH:33]=[CH:32][N:31]=1)C1C=CC=CC=1.NC1C2C(=CC(C=CC(O)=O)=CC=2)C=CN=1.Cl.[CH3:62][O:63][C:64](=[O:76])[CH2:65][C:66]([N:68]1[CH2:73][CH2:72][CH:71]([NH:74][CH3:75])[CH2:70][CH2:69]1)=[O:67]>>[CH3:62][O:63][C:64](=[O:76])[CH2:65][C:66]([N:68]1[CH2:69][CH2:70][CH:71]([N:74]([C:42](=[O:44])[CH:41]=[CH:40][C:36]2[CH:35]=[C:34]3[C:39](=[CH:38][CH:37]=2)[C:30]([NH2:29])=[N:31][CH:32]=[CH:33]3)[CH3:75])[CH2:72][CH2:73]1)=[O:67]Participants
5
Reactant 4
Product 1
Procedure
Using the method described in example 81a N-(6-formyl-1-isoquinolinyl)benzamide (1f) was transformed into 3-(1-(benzylamino)-6-isoquinolinyl)acrylic acid. This compound was used to prepare 3-(1-amino-6-isoquinolinyl)acrylic acid according to the procedure described in example 81b. Reaction of 3-(1-amino-6-isoquinolinyl)acrylic acid with 3-(4-(methylamino)piperidin-1-yl)-3-oxopropionic acid methyl ester hydrochloride according to the procedures described in example 81e yielded the title compound. NMR (CDCl3) δ:1.8 (4H, m), 2.7 (1H, m), 3.0 (3H, s), 3.2 (1H, m), 3.5 (2H, d), 3.7 (3H, s), 3.9 (1H, br d), 4.8 (2H, m), 4.9 (2H, br s), 7.0 (1H, d), 7.5 (1H, d), 7.65 (1H, d), 7.8 (3H, m), 8.0 (1H, d).
Sources & evidence
- ORD record
- ord-a874c504d0fc4cfbaaa6cddcf80be08b
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797710B2
Reaction notes
Loading…