HCID 178457814, compound → HCID 178457805, compound

HRID 518770Notes

Reaction equation

HRID 518770 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[NH:12][C@@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[F:25][C:26]1[CH:59]=[CH:58][C:29]([C:30](/[N:32]=[C:33]2/N([C@H]3CC[C@@H](C(=O)NC(C)C)CC3)C3C=C(S(C)(=O)=O)N=CC=3N/2)=[O:31])=[CH:28][CH:27]=1>>[F:25][C:26]1[CH:27]=[CH:28][C:29]([C:30](/[N:32]=[C:33]2\[NH:1][C:2]3[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=3[N:12]\2[C@H:13]2[CH2:14][CH2:15][C@@H:16]([C:19](=[O:20])[NH:21][CH:22]([CH3:24])[CH3:23])[CH2:17][CH2:18]2)=[O:31])=[CH:58][CH:59]=1

Participants

3

Reactant 2

HCID 178457814HCID 178457814, compoundHCID 178457866HCID 178457866, compound

Product 1

HCID 178457805HCID 178457805, compound

Procedure

The title compound was prepared from cis-4-(2-amino-5-(methylsulfonyl) phenylamino)-N-isopropylcyclohexanecarboxamide using a method analogous to that used in the preparation of (E)-4-fluoro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(methylsulfonyl)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide, as an off-white solid (0.111 g, 75% yield). MS, m/z (C25H29FN4O4S): calcd, 500.59. found 501.2 [M+H]. 1H NMR (400 MHz, DMSO-d6) d ppm 1.09 (d, J=6.55 Hz, 6H) 1.62-1.81 (m, 4H) 2.14 (m, J=13.10 Hz, 2H) 2.51-2.57 (m, 2H) 2.75-2.91 (m, 2H) 3.28 (s, 3H) 3.99-4.10 (m, 1H) 4.72-4.88 (m, 1H) 7.22-7.29 (m, 2H) 7.64 (d, J=7.73 Hz, 1H) 7.68-7.79 (m, 2H) 8.23-8.27 (m, 1H) 8.32-8.40 (m, 2H) 13.04 (br. s, 1H). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (d, J=6.55 Hz, 6H) 1.62-1.81 (m, 4H) 2.09-2.19 (m, 2H) 2.51-2.57 (m, 2H) 2.75-2.91 (m, 2H) 3.28 (s, 3H) 4.05 (sxt, J=6.94 Hz, 1H) 4.72-4.88 (m, 1H) 7.25 (s, 2H) 7.64 (d, J=7.73 Hz, 1H) 7.68-7.79 (m, 2H) 8.23-8.27 (m, 1H) 8.32-8.40 (m, 2H) 13.04 (br. s, 1H).

Sources & evidence

ORD record
ord-c612c2eca7dc43ff86c1bf07a5025050
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…