tert-Butyl {2-amino-1-[2-(trifluoromethyl)phenyl]ethyl}carbamate → tert-Butyl {2-({[3-(5-chloro-2-thienyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}amino)-1-[2-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 709168Notes

Reaction equation

HRID 709168 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:10](=[O:20])[N:9]([CH2:21][C:22](O)=[O:23])[N:8]=2)=[CH:4][CH:3]=1.[NH2:25][CH2:26][CH:27]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([F:37])([F:36])[F:35]>>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:10](=[O:20])[N:9]([CH2:21][C:22]([NH:25][CH2:26][CH:27]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:42])([CH3:44])[CH3:43])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])=[O:23])[N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 43099850tert-Butyl {2-amino-1-[2-(trifluoromethyl)phenyl]ethyl}carbamateHCID 58011885HCID 58011885, compound

Product 1

HCID 56848686tert-Butyl {2-({[3-(5-chloro-2-thienyl)-4-(2-fluorobenzyl)-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, 54 mg (146 μmol) of [3-(5-chloro-2-thienyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid [for the preparation see Example 154A in WO 2007/134862] were reacted with 49 mg (161 μmol) of tert-butyl {2-amino-1-[2-(trifluoromethyl)phenyl]ethyl}carbamate. This gave 64 mg (67% of theory) of the title compound.

Sources & evidence

ORD record
ord-5be2340e681044db97fefd1777fd87ab
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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