5-Methyl-2-pyridinesulfonamide → 5-Chloro-2-(4-fluorophenoxy)-N-{(1S)-1-[4-({[(5-methylpyridin-2-YL)sulfonyl]amino}carbonyl)phenyl]ethyl}nicotinamide

HRID 1293274

Reaction equation

HRID 1293274 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH:18][C@H:19]([C:21]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=2)[CH3:20])=[O:17])[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:30][C:31]1[CH:32]=[CH:33][C:34]([S:37]([NH2:40])(=[O:39])=[O:38])=[N:35][CH:36]=1>>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)=[C:4]([CH:3]=1)[C:16]([NH:18][C@H:19]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([NH:40][S:37]([C:34]2[CH:33]=[CH:32][C:31]([CH3:30])=[CH:36][N:35]=2)(=[O:39])=[O:38])=[O:27])=[CH:28][CH:29]=1)[CH3:20])=[O:17]

Participants

3

Reactant 2

HCID 36141995-Methyl-2-pyridinesulfonamideHCID 116830884-[(1S)-1-({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)ethyl]benzoic acid

Product 1

HCID 589053715-Chloro-2-(4-fluorophenoxy)-N-{(1S)-1-[4-({[(5-methylpyridin-2-YL)sulfonyl]amino}carbonyl)phenyl]ethyl}nicotinamide

Procedure

The title compound was prepared according to the procedure described in step 1 of Example 103 from 4-[(1S)-1-({[5-chloro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoic acid (step 5 of Example 44) and 5-methylpyridine-2-sulfonamide: 1H-NMR (DMSO-d6) δ 8.95 (1H, d, J=8.6 Hz), 8.38 (1H, br.s), 8.26 (1H, d, J=2.6 Hz), 8.10 (1H, d, J=2.6 Hz), 7.92–7.70 (4H, m), 7.40 (2H, d, J=7.9 Hz), 7.30–7.23 (4H, m), 5.22–5.08 (1H, m), 2.34 (3H, s), 1.44 (3H, d, J=6.8 Hz); MS (ESI) m/z 569 (M+H)+, 567 (M−H)−.

Sources & evidence

ORD record
ord-8aa4b6e655cb4404bd7b8f6c9d298b11
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Linked notes

Loading…