1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-({1-[4-(5-Trichloromethyl-[1,2,4]oxadiazol-3-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

HRID 2388357Notes

Reaction equation

HRID 2388357 reaction equation
CCN=C=NCCCN(C)C.[Cl:12][C:13]([Cl:31])([Cl:30])[C:14]1[O:18][N:17]=[C:16]([CH:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:28][CH:27]([NH2:29])[CH2:26]3)[CH2:21][CH2:20]2)[N:15]=1.[F:32][C:33]([F:48])([F:47])[C:34]1[CH:35]=[C:36]([CH:44]=[CH:45][CH:46]=1)[C:37]([NH:39][CH2:40][C:41](O)=[O:42])=[O:38]>>[Cl:31][C:13]([Cl:30])([Cl:12])[C:14]1[O:18][N:17]=[C:16]([CH:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:28][CH:27]([NH:29][C:41]([CH2:40][NH:39][C:37](=[O:38])[C:36]4[CH:44]=[CH:45][CH:46]=[C:34]([C:33]([F:48])([F:32])[F:47])[CH:35]=4)=[O:42])[CH2:26]3)[CH2:21][CH2:20]2)[N:15]=1

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acidHCID 595418221-[4-(5-Trichloromethyl-[1,2,4]oxadiazol-3-yl)-cyclohexyl]-azetidin-3-ylamine

Product 1

HCID 46946854N-({1-[4-(5-Trichloromethyl-[1,2,4]oxadiazol-3-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

Procedure

The title compound was prepared by the EDCI coupling of 1-[4-(5-trichloromethyl-[1,2,4]oxadiazol-3-yl)-cyclohexyl]-azetidin-3-ylamine (as prepared in the previous step) and (3-trifluoromethyl-benzoylamino)-acetic acid (Bionet Building Blocks). Purification by HPLC gave cis and trans isomers.

Workup

  1. customPurification by HPLC
  2. customgave cis and trans isomers

Sources & evidence

ORD record
ord-f72a67e1a8ea42729b24c102ce245a31
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

Loading…