m-(Trifluoromethyl)cinnamic acid → 2-[4-(1H-Indol-3-yl)-cyclohexylamino]-2-[1-(trans-3-{trifluoromethyl}-cinnamoyl)piperidin-4-yl]-acetamide

HRID 1410528Notes

Reaction equation

HRID 1410528 reaction equation
Cl.Cl.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:20]([NH2:22])=[O:21])[CH2:14][CH2:13]2)=[CH:4]1.[F:29][C:30]([F:43])([F:42])[C:31]1[CH:32]=[C:33]([CH:39]=[CH:40][CH:41]=1)/[CH:34]=[CH:35]/[C:36](O)=[O:37]>>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([CH:23]3[CH2:24][CH2:25][N:26]([C:36](=[O:37])/[CH:35]=[CH:34]/[C:33]4[CH:39]=[CH:40][CH:41]=[C:31]([C:30]([F:42])([F:43])[F:29])[CH:32]=4)[CH2:27][CH2:28]3)[C:20]([NH2:22])=[O:21])[CH2:14][CH2:13]2)=[CH:4]1

Participants

3

Reactant 2

HCID 719451m-(Trifluoromethyl)cinnamic acidHCID 677751942-[4-(1H-Indol-3-yl)-cyclohexylamino]-2-piperidin-4-yl-acetamide dihydrochloride

Product 1

HCID 573438162-[4-(1H-Indol-3-yl)-cyclohexylamino]-2-[1-(trans-3-{trifluoromethyl}-cinnamoyl)piperidin-4-yl]-acetamide

Procedure

The title compound was prepared from the product of Example 1, step J (142 mg, 0.333 mmol), and trans-3-(trifluoromethyl)-cinnamic acid, by the method of Example 1, step K, giving a gold solid that was mostly the more polar cyclohexyl diastereomer by LCMS. Mass spectrum (LCMS, ESI pos.) calcd. for C31H35F3N4O2: 553 (M+H). Found: 553.2.

Workup

  1. customgiving a gold solid that

Sources & evidence

ORD record
ord-7b908c606f384ef28389f802a6784a8e
Source dataset
uspto-grants-2014_12
Patent number
US08921559B2

Reaction notes

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