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

HRID 1893321Notes

Reaction equation

HRID 1893321 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].[OH:40][C:41]1[CH:42]=[C:43]([C:50]([F:53])([F:52])[F:51])[CH:44]=[C:45]([CH:49]=1)[C:46](O)=[O:47]>>[OH:40][C:41]1[CH:49]=[C:45]([CH:44]=[C:43]([C:50]([F:51])([F:52])[F:53])[CH:42]=1)[C:46]([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:47]

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27831463-hydroxy-5-(trifluoromethyl)benzoic AcidHCID 866466812-Amino-N-[1-(4-phenyl-cyclohexyl)-azetidin-3-yl]-acetamide TFA salt

Product 1

HCID 497634593-Hydroxy-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-hydroxy-3-trifluoromethyl-benzoic acid (Alfa Aesar) using the procedure described in Step F of Example 1.

Sources & evidence

ORD record
ord-782f2c73230243518eec9315318a700e
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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