2-methyl-N-[5-(4-piperidinyl)-3-pyridinyl]propanamide → N-{5-[1-(3-{[bis(4-fluorophenyl)acetyl]amino}propyl)-4-piperidinyl]-3-pyridinyl}-2-methylpropanamide

HRID 1269338Notes

Reaction equation

HRID 1269338 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:22])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.[CH3:23][CH:24]([CH3:40])[C:25]([NH:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:33]=1)=[O:26]>>[F:14][C:11]1[CH:12]=[CH:13][C:8]([CH:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:6]([NH:5][CH2:4][CH2:3][CH2:2][N:37]2[CH2:38][CH2:39][CH:34]([C:32]3[CH:33]=[C:28]([NH:27][C:25](=[O:26])[CH:24]([CH3:23])[CH3:40])[CH:29]=[N:30][CH:31]=3)[CH2:35][CH2:36]2)=[O:22])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 184468432-methyl-N-[5-(4-piperidinyl)-3-pyridinyl]propanamideHCID 18446872N-(3-bromopropyl)-2,2-bis(4-fluorophenyl)acetamide

Product 1

HCID 10414764N-{5-[1-(3-{[bis(4-fluorophenyl)acetyl]amino}propyl)-4-piperidinyl]-3-pyridinyl}-2-methylpropanamide

Procedure

Example 172 was prepared from N-(3-bromopropyl)-2,2-bis(4-fluoro phenyl) acetamide and 2-methyl-N-[5-(4-piperidinyl)-3-pyridinyl]propanamide according to the procedures described in Scheme 14: 1H NMR (400 MHz, CDCl3) δ 8.39 (s, 1 H), 8.19 (s, 1 H), 8.17 (S, 1 H), 7.95 (s, 1 H), 7.31–7.20 (m, 5 H), 7.04–6.94 (m, 4 H), 4.82 (s, 1 H), 3.46–3.35 (m, 2 H), 2.98–2.92 (m, 2 H), 2.62–2.48 (m, 2 H), 2.48–2.38 (m, 2 H), 2.09–1.95 (m, 2 H), 1.87–1.76 (m, 2 H), 1.76–1.55 (m, 4 H), 1.25 (d, 6 H, J=7.6 Hz); ESMS m/e: 535.4 (M+H)+.

Sources & evidence

ORD record
ord-78b29dae8f8046e08472567cb7703206
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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