Dodecylamine → N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy) phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

HRID 418661

Reaction equation

HRID 418661 reaction equation
CCCCCCCCCCCC[NH2:13].[F:14][C:15]1[CH:16]=[C:17](NC(=O)CC(NC2C=CC=CC=2)=O)[CH:18]=[CH:19][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[CH:28]=[C:29]([C:31]3[N:32]=[CH:33][N:34]([CH3:36])[CH:35]=3)[S:30][C:23]=12.O=C(NC1C=CC=CC=1)CC(O)=O.[F:63][C:64]1[CH:69]=[CH:68][C:67]([NH:70][C:71]([C:73]2([C:76]([OH:78])=O)[CH2:75][CH2:74]2)=[O:72])=[CH:66][CH:65]=1>>[F:14][C:15]1[CH:16]=[C:17]([N:70]([C:67]2[CH:66]=[CH:65][C:64]([F:63])=[CH:69][CH:68]=2)[C:71]([C:73]2([C:76]([NH2:13])=[O:78])[CH2:74][CH2:75]2)=[O:72])[CH:18]=[CH:19][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[CH:28]=[C:29]([C:31]3[N:32]=[CH:33][N:34]([CH3:36])[CH:35]=3)[S:30][C:23]=12

Participants

5

Reactant 4

HCID 13583DodecylamineHCID 2565932-(Phenylcarbamoyl)acetic acidHCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic AcidHCID 44565164N1-(3-fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-phenylmalonamide

Product 1

HCID 56952684N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy) phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamideYield 24%

Procedure

Starting from the amine 12 (scheme 3) and following the procedure described above for the compound 5c (example 3, scheme 3), but replacing acid 1 for the acid 181, title compound 180 was obtained in 24% yield. 1H NMR (DMSO-d6) δ (ppm): 10.39 (s, 1H), 10.01 (s, 1H), 8.42 (d, J=5.5 Hz, 1H), 7.87 (dd, J=14.2 and 2.4 Hz, 1H), 7.85 (d, 1H, J=1.2 Hz), 7.70 (d, 1H, J=1.1 Hz), 7.66 (s, 1H), 7.64-7.61 (m, 2H), 7.50 (dd, J=2.0 and 8.8 Hz, 1H), 7.43 (t, 1H, J=8.8 Hz), 7.16-7.11 (m, 2H), 6.55 (d, 1H, J=5.5 Hz), 3.71 (s, 3H), 1.44 (m, 4H). MS (m/z): 546.0 (M+H).

Sources & evidence

ORD record
ord-b484567e1f1f497088551a40de51481d
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Linked notes

Loading…