(Diethylamino)sulfur trifluoride → 3-fluoro-N-((6-(di flu oromethyl)-5-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)pyridin-3-yl)methyl)-2,2-dimethylpropanamide

HRID 59577Notes

Reaction equation

HRID 59577 reaction equation
[F:1][CH:2]([F:34])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:17])[C:12]([CH3:16])([CH3:15])[CH2:13]O)=[CH:5][C:4]=1[C:18]1[NH:22][C:21](=[O:23])[N:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[N:19]=1.CCN(S(F)(F)[F:41])CC>C(Cl)Cl>[F:41][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]([NH:10][CH2:9][C:6]1[CH:7]=[N:8][C:3]([CH:2]([F:1])[F:34])=[C:4]([C:18]2[NH:22][C:21](=[O:23])[N:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[N:19]=2)[CH:5]=1)=[O:17]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 136492426N-((6-(difluoromethyl)-5-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)pyridin-3-yl)methyl)-3-hydroxy-2,2-dimethylpropanamide

Product 1

HCID 1364923753-fluoro-N-((6-(di flu oromethyl)-5-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)pyridin-3-yl)methyl)-2,2-dimethylpropanamideYield 8.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by following the procedure as described in step-2 of Example-134 by using N-((6-(difluoromethyl)-5-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)pyridin-3-yl)methyl)-3-hydroxy-2,2-dimethylpropanamide (0.060 g, 0.12 mmol), DAST (0.060 g, 0.37 mmol), DCM (10 mL) to afford 0.005 g the desired product. 1H NMR (300 MHz, DMSO d6): δ 0.80 (br s, 6H), 4.22 (br s, 1H), 4.38-4.42 (m, 3H), 7.41-7.66 (m, 3H), 7.95 (br s, 1H), 8.08-8.11 (m, 211), 8.61 (s, 1H); MS (m/z): 488.23 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-af28600a6815407588e25ccdf01c1230
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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