Bis(4-chlorophenyl)acetic acid → N-{6-[1-(3-{[bis(4-chlorophenyl)acetyl]amino}propyl)-4-piperidinyl]-2-pyridinyl}-2-methylpropanamide

HRID 1269228Notes

Reaction equation

HRID 1269228 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[N:34]=[C:33]([NH:35][C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])[CH:32]=[CH:31][CH:30]=2)[CH2:25][CH2:24]1>>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]([NH:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([C:29]3[N:34]=[C:33]([NH:35][C:36](=[O:40])[CH:37]([CH3:38])[CH3:39])[CH:32]=[CH:31][CH:30]=3)[CH2:27][CH2:28]2)=[O:11])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 6730Bis(4-chlorophenyl)acetic acidHCID 21957182N-{6-[1-(3-aminopropyl)-4-piperidinyl]-2-pyridinyl}2-methylpropanamide

Product 1

HCID 21957215N-{6-[1-(3-{[bis(4-chlorophenyl)acetyl]amino}propyl)-4-piperidinyl]-2-pyridinyl}-2-methylpropanamide

Procedure

Example 50 was prepared from bis(4-chlorophenyl)acetic acid and N-{6-[1-(3-aminopropyl)-4-piperidinyl]-2-pyridinyl}-2-methylpropanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.06 (d, 1H, J=8.0 Hz), 7.96 (br s, 1H), 7.77 (s, 1H), 7.64 (t, 1H, J=8.4 Hz), 7.31–7.26 (m, 8H), 6.88 (dd, 1H, J=0.8, 7.6 Hz), 4.84 (s, 1H), 3.39 (dd, 2H, J=5.6, 11.6 Hz), 2.99 (d, 2H, J=11.6 Hz), 2.59 (m, 1H), 2.47 (t, 2H, J=6.0 Hz), 2.28 (m, 1H), 2.07–2.00 (m, 2H), 1.89 (dd, 2H, J=2.0, 12.4 Hz), 1.76–1.67 (m, 4H), 1.14 (d, 6H, J=6.8 Hz); ESMS m/e: 567.3 (M+H)+.

Sources & evidence

ORD record
ord-0c3374f8fdb446d4b4602155f611a85d
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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