1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-Nitro-N-{[1-(4-phenyl-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-5-trifluoromethyl-benzamide

HRID 1893320Notes

Reaction equation

HRID 1893320 reaction equation
CCN=C=NCCCN(C)C.OC(C(F)(F)F)=O.[NH2:19][CH2:20][C:21]([NH:23][CH:24]1[CH2:27][N:26]([CH:28]2[CH2:33][CH2:32][CH:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:30][CH2:29]2)[CH2:25]1)=[O:22].[N+:40]([C:43]1[CH:44]=[C:45]([C:52]([F:55])([F:54])[F:53])[CH:46]=[C:47]([CH:51]=1)[C:48](O)=[O:49])([O-:42])=[O:41]>>[N+:40]([C:43]1[CH:51]=[C:47]([CH:46]=[C:45]([C:52]([F:53])([F:54])[F:55])[CH:44]=1)[C:48]([NH:19][CH2:20][C:21](=[O:22])[NH:23][CH:24]1[CH2:27][N:26]([CH:28]2[CH2:33][CH2:32][CH:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:30][CH2:29]2)[CH2:25]1)=[O:49])([O-:42])=[O:41]

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acidHCID 866466812-Amino-N-[1-(4-phenyl-cyclohexyl)-azetidin-3-yl]-acetamide TFA salt

Product 1

HCID 497634563-Nitro-N-{[1-(4-phenyl-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared as a white solid from the EDCI coupling of 2-amino-N-[1-(4-phenyl-cyclohexyl)-azetidin-3-yl]-acetamide TFA salt (as prepared in Step D of Example 66) and 5-nitro-3-trifluoromethyl-benzoic acid (Aldrich) using the procedure described in Step F of Example 1.

Sources & evidence

ORD record
ord-0e39a08639794114b4a6c643cb9ee3b7
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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