[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid → tert-Butyl {2-({[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetyl}amino)-1-[2-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 709166Notes

Reaction equation

HRID 709166 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18](O)=[O:19])[N:9]=2)=[CH:4][CH:3]=1.[NH2:21][CH2:22][CH:23]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([F:33])([F:32])[F:31]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:21][CH2:22][CH:23]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:38])([CH3:40])[CH3:39])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:33])([F:32])[F:31])=[O:19])[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 42632357[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acidHCID 43099850tert-Butyl {2-amino-1-[2-(trifluoromethyl)phenyl]ethyl}carbamate

Product 1

HCID 66635364tert-Butyl {2-({[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetyl}amino)-1-[2-(trifluoromethyl)phenyl]ethyl}carbamate

Procedure

Analogously to the procedure of Example 63, 43 mg (146 μmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid [for the preparation see Example 88A in WO 2007/134862] were reacted with 49 mg (161 μmol) of tert-butyl {2-amino-1-[2-(trifluoromethyl)phenyl]ethyl}carbamate. This gave 59 mg (69% of theory) of the title compound.

Sources & evidence

ORD record
ord-5cfa2e5c5cc74aa19903ae8f2f3a2340
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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