N-(2-Methoxy-phenyl)-malonamic acid → N1-(3-fluoro-4-(2-(1-propyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamide

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17]([C:19]3[N:20]=[CH:21][N:22]([CH2:24][CH2:25][CH3:26])[CH:23]=3)[S:18][C:11]=12)[NH2:5].FC1C=CC=CC=1NC(=O)CC(O)=O.[CH3:41][O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[NH:49][C:50](=[O:55])[CH2:51][C:52](O)=[O:53]>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:52](=[O:53])[CH2:51][C:50]([NH:49][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[O:42][CH3:41])=[O:55])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17]([C:19]3[N:20]=[CH:21][N:22]([CH2:24][CH2:25][CH3:26])[CH:23]=3)[S:18][C:11]=12

Participants

Reactant 3

HCID 12664594N-(2-Methoxy-phenyl)-malonamic acid

HCID 164811562-[(2-Fluorophenyl)carbamoyl]acetic acid

HCID 587904093-Fluoro-4-(2-(1-propyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline

Product 1

HCID 16042165N1-(3-fluoro-4-(2-(1-propyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamide

Procedure

Title compound 134 (scheme 38) was obtained similarly to the compound 130 (example 49, scheme 38) starting from the amine 133 and replacing the acid 29 with the acid 27. 1H NMR (DMSO-d6). δ (ppm): 10.58 (s, 1H), 9.64 (s, 1H), 8.43 (d, J=5.6 Hz, 1H), 8.07 (dd, J=1.2 and 8.8 Hz, 1H), 7.94 (d, J=1.2 Hz, 1H), 7.87 (dd, J=1.6 and 12.8 Hz, 1H), 7.77 (d, J=1.2 Hz, 1H), 7.68 (s, 1H), 7.49 (t, J=8.8 Hz, 1H), 7.43 (dd, J=2.0 and 8.8 Hz, 1H), 7.11-7.04 (m, 2H), 6.92 (ddd, J=2.4, 6.4 and 8.0 Hz, 1H), 6.58 (d, J=5.6 Hz, 1H), 3.98 (t, J=7.2 Hz, 2H), 3.86 (s, 3H), 3.64 (s, 2H), 1.78 (sex, J=7.2 Hz, 2H), 0.87 (t, J=7.2 Hz, 3H). MS (m/z): 559.2 (M+H).