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

HRID 418644Notes

Reaction equation

HRID 418644 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

4

Reactant 3

HCID 12664594N-(2-Methoxy-phenyl)-malonamic acidHCID 164811562-[(2-Fluorophenyl)carbamoyl]acetic acidHCID 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).

Sources & evidence

ORD record
ord-2b207d703cfb49fdae8856e8c5c5765f
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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