Bis(4-chlorophenyl)acetic acid → Isopropyl 3-[1-(3-{[bis(4-chlorophenyl)acetyl]amino}propyl)-4-piperidinyl]phenylcarbamate

HRID 2213509Notes

Reaction equation

HRID 2213509 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[CH:30]=[C:31]([NH:35][C:36](=[O:41])[O:37][CH:38]([CH3:40])[CH3:39])[CH:32]=[CH:33][CH:34]=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[CH2:28][CH2:27][CH:26]([C:29]3[CH:30]=[C:31]([NH:35][C:36](=[O:41])[O:37][CH:38]([CH3:39])[CH3:40])[CH:32]=[CH:33][CH:34]=3)[CH2:25][CH2:24]2)=[O:11])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 6730Bis(4-chlorophenyl)acetic acidHCID 21957208Isopropyl 3-[1-(3-aminopropyl)-4-piperidinyl]phenylcarbamate

Product 1

HCID 21957199Isopropyl 3-[1-(3-{[bis(4-chlorophenyl)acetyl]amino}propyl)-4-piperidinyl]phenylcarbamate

Procedure

Example 143 was prepared from bis(4-chlorophenyl)acetic acid and isopropyl 3-[1-(3-aminopropyl)-4-piperidinyl]phenylcarbamate according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.46 (s, 1H), 7.37 (s, 1H), 7.23–7.10 (m, 9H), 7.00 (d, 1H, J=7.9 Hz), 6.80 (d, 1H, J=7.4 Hz), 6.60 (s, 1H), 4.88 (septet, 1H, J=6.2 Hz), 4.68 (s, 1H), 4.05 (q, 1H, J=7.3 Hz), 3.32 (q, 2H, J=5.9 Hz), 2.90–2.83 (m, 2H), 2.44–2.32 (m, 3H), 1.94–1.86 (m, 2H), 1.78–1.70 (m, 2H), 1.60 (quintet, 2H, J=6.4 Hz), 1.56–1.43 (m, 1H), 1.22 (d, 6H, J=6.2 Hz); ESMS m/e: 582.2 (M+H)+.

Sources & evidence

ORD record
ord-20cb7b43e8124537974bce83a40c43c7
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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