[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid → 2-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{2-hydroxy-1-[3-(trifluoromethyl)phenyl]ethyl}acetamide

HRID 220706Notes

Reaction equation

HRID 220706 reaction equation
ClC1C=CC(C2N(C[C@H](O)C(F)(F)F)C(=O)N(CC(NC(C3C=CC=C(F)C=3F)CO)=O)N=2)=CC=1.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[N:47]([CH:48]3[CH2:50][CH2:49]3)[C:46](=[O:51])[N:45]([CH2:52][C:53](O)=[O:54])[N:44]=2)=[CH:39][CH:38]=1.FC(F)(F)C(O)=O.[NH2:63][CH:64]([C:67]1[CH:72]=[CH:71][CH:70]=[C:69]([C:73]([F:76])([F:75])[F:74])[CH:68]=1)[CH2:65][OH:66]>>[Cl:36][C:37]1[CH:38]=[CH:39][C:40]([C:43]2[N:47]([CH:48]3[CH2:50][CH2:49]3)[C:46](=[O:51])[N:45]([CH2:52][C:53]([NH:63][CH:64]([C:67]3[CH:72]=[CH:71][CH:70]=[C:69]([C:73]([F:74])([F:75])[F:76])[CH:68]=3)[CH2:65][OH:66])=[O:54])[N:44]=2)=[CH:41][CH:42]=1

Participants

4

Reactant 3

HCID 42632357[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acidHCID 595369172-{3-(4-Chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N-[1-(2,3-difluorophenyl)-2-hydroxyethyl]acetamideHCID 866466322-Amino-2-[3-(trifluoromethyl)phenyl]ethanol trifluoroacetate

Product 1

HCID 469280742-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{2-hydroxy-1-[3-(trifluoromethyl)phenyl]ethyl}acetamide

Procedure

In the same way as for the compound from Example 95, 48 mg (0.16 mmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid (for preparation see WO 2007/134862, Example 88A) and 58 mg (0.18 mmol) of the compound from Example 91A were reacted. This gave 61 mg (77% of theory) of the target compound.

Sources & evidence

ORD record
ord-b04a60fd3fda4385b133f0ab4b59f50d
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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