N-(2-Methoxy-phenyl)-malonamic acid → n1-(3-Fluoro-4-(2-(1-methyl-1h-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-n3-(2-fluoroxyphenyl)malonamide

HRID 418593Notes

Reaction equation

HRID 418593 reaction equation
[F:1]C1C=C(N)C=CC=1OC1C=CN=C2C=C(C3N(C)C=CN=3)SC=12.[F:25][C:26]1[CH:27]=[C:28]([NH:48][C:49](=[O:62])[CH2:50][C:51]([NH:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=2[O:60]C)=[O:52])[CH:29]=[CH:30][C:31]=1[O:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]2[CH:39]=[C:40]([C:42]3[N:43]([CH3:47])[CH:44]=[CH:45][N:46]=3)[S:41][C:34]=12.COC1C=CC=CC=1NC(=O)CC(O)=O.FC1C=CC=CC=1NC(=O)CC(O)=O>>[F:25][C:26]1[CH:27]=[C:28]([NH:48][C:49](=[O:62])[CH2:50][C:51]([NH:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=2[O:60][F:1])=[O:52])[CH:29]=[CH:30][C:31]=1[O:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]2[CH:39]=[C:40]([C:42]3[N:43]([CH3:47])[CH:44]=[CH:45][N:46]=3)[S:41][C:34]=12

Participants

5

Reactant 4

HCID 12664594N-(2-Methoxy-phenyl)-malonamic acidHCID 16040869N1-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamideHCID 164811562-[(2-Fluorophenyl)carbamoyl]acetic acidHCID 594244803-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

Product 1

HCID 66648945n1-(3-Fluoro-4-(2-(1-methyl-1h-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-n3-(2-fluoroxyphenyl)malonamideYield 5%

Procedure

Starting from the amine 9 and following the procedure described above for the compound 28a (example 8, step 2) but substituting acid 27 for the acid 29, title compound 30a was obtained as a white solid in 5% yield. 1H NMR (DMSO-d6) δ (ppm): 10.56 (s, 1H), 10.04 (s, 1H), 8.50 (d. 1H), 7099-7.95 (m, 1H), 7.88 (s, 1H), 7.86 (dd, 1H), 7.50 (t, 2H) 7.42 (dd, 1H), 7.40 (s, 1H), 7.29-7.24 (m, 1H), 7.17-7.14 (m, 1H), 7.03 (s, 1H), 6.69 (d. 1H), 4.00 (s, 3H), 3.64 (s, 2H). MS (m/z): 520.1 (M+H).

Sources & evidence

ORD record
ord-f1a32dd94d0841169e873528d5ebd68b
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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