4-Methyl-alpha-(4-methylphenyl)benzeneacetic acid → N-{3-[1-(3-{[2,2-bis(4-methylphenyl)acetyl]amino}propyl)-4-piperidinyl]phenyl}cyclopropanecarboxamide

HRID 1269288Notes

Reaction equation

HRID 1269288 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[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]([CH:38]3[CH2:40][CH2:39]3)=[O:37])[CH:32]=[CH:33][CH:34]=2)[CH2:25][CH2:24]1>>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[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]([CH:38]4[CH2:40][CH2:39]4)=[O:37])[CH:32]=[CH:33][CH:34]=3)[CH2:25][CH2:24]2)=[O:11])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 303144-Methyl-alpha-(4-methylphenyl)benzeneacetic acidHCID 21957166N-{3-[1-(3-aminopropyl)4-piperidinyl]phenyl}cyclopropanecarboxamide

Product 1

HCID 11756545N-{3-[1-(3-{[2,2-bis(4-methylphenyl)acetyl]amino}propyl)-4-piperidinyl]phenyl}cyclopropanecarboxamide

Procedure

Example 111 was prepared from bis(4-methylphenyl)acetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}cyclo propanecarboxamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.24–8.04 (br, 1H), 8.04–7.95 (br, 1H), 7.59–6.92 (m, 10H), 6.90–6.76 (m, 1H), 4.98–4.82 (br, 1H), 4.72 (s, 1H), 3.42–3.25 (m, 2H), 3.25–3.08 (m, 2H), 2.75–2.56 (m, 2H), 2.56–2.40 (m, 1H), 2.35–2.17 (m, 2H), 2.26 (s, 6H), 1.99–1.68 (m, 6H), 1.57–1.44 (m, 1H), 1.12–0.99 (m, 2H), 0.87–0.70 (m, 2H); ESMS m/e: 524.3 (M+H)+; Anal. Calc. for (HCl salt) C34H42ClF2N3O2.0.29CHCl3: C, 69.23; H, 7.16; N, 7.06. Found: C, 68.96; H, 7.35; N, 7.31.

Sources & evidence

ORD record
ord-588120569c9843159156f5670181f336
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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