2-Fluorocinnamic acid → 2-[4-(1H-Indol-3-yl)-cyclohexylamino]-2-[1-(trans-2-fluorocinnamoyl)-piperidin-4-yl]-acetamide

HRID 1410527Notes

Reaction equation

HRID 1410527 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]1[CH:40]=[CH:39][CH:38]=[CH:37][C:31]=1/[CH:32]=[CH:33]/[C:34](O)=[O:35]>>[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:34](=[O:35])/[CH:33]=[CH:32]/[C:31]4[CH:37]=[CH:38][CH:39]=[CH:40][C:30]=4[F:29])[CH2:27][CH2:28]3)[C:20]([NH2:22])=[O:21])[CH2:14][CH2:13]2)=[CH:4]1

Participants

3

Reactant 2

HCID 7358332-Fluorocinnamic acidHCID 677751942-[4-(1H-Indol-3-yl)-cyclohexylamino]-2-piperidin-4-yl-acetamide dihydrochloride

Product 1

HCID 573442972-[4-(1H-Indol-3-yl)-cyclohexylamino]-2-[1-(trans-2-fluorocinnamoyl)-piperidin-4-yl]-acetamide

Procedure

The title compound was prepared from the product of Example 1, step J, and trans-2-fluoro-cinnamic acid, by the method of Example 1, step K, giving a solid that was a mixture of cyclohexyl diastereomers by LCMS. Mass spectrum (LCMS, ESI pos.) calcd. for C30H35FN4O2: 502 (M+H). Found: 503

Workup

  1. customgiving a solid
  2. additiona mixture of cyclohexyl diastereomers by LCMS

Sources & evidence

ORD record
ord-ab0c2fecfda34e119ec9a11ed2427ae5
Source dataset
uspto-grants-2014_12
Patent number
US08921559B2

Reaction notes

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