Diisopropylethylamine → 5-(4-Chlorophenyl)-4-(4-methoxybenzyl)-2-({1-[2-(trifluoromethyl)benzyl]-1H-1,2,4-triazol-5-yl}-sulfonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714723Notes

Reaction equation

HRID 714723 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[C:10](=[O:21])[N:11]([S:13]([C:16]3[NH:20][N:19]=[CH:18][N:17]=3)(=[O:15])=[O:14])[N:12]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[F:40][C:41]([F:51])([F:50])[C:42]1[CH:49]=[CH:48][CH:47]=[CH:46][C:43]=1[CH2:44]Br>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[C:10](=[O:21])[N:11]([S:13]([C:16]3[N:20]([CH2:44][C:43]4[CH:46]=[CH:47][CH:48]=[CH:49][C:42]=4[C:41]([F:40])([F:50])[F:51])[N:19]=[CH:18][N:17]=3)(=[O:15])=[O:14])[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 699400535-(4-Chlorophenyl)-4-(4-methoxybenzyl)-2-(1H-1,2,4-triazol-5-ylsulfonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 674070755-(4-Chlorophenyl)-4-(4-methoxybenzyl)-2-({1-[2-(trifluoromethyl)benzyl]-1H-1,2,4-triazol-5-yl}-sulfonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

334 mg (0.75 mmol) of the compound from Example 94A were dissolved in 5 ml of dichloromethane, and 154 μl (0.93 mmol) of N,N-diisopropylethylamine were added. 223 mg (0.93 mmol) of 2-(trifluoromethyl)benzyl bromide dissolved in 0.5 ml of dichloromethane were then added, and the mixture was stirred at RT for 20 h. For work-up, the mixture was concentrated under reduced pressure and the crude product was purified chromatographically [Method 19]. This gave 245 mg (54% of theory) of the target compound.

Workup

  1. additionwere then added
  2. concentrationFor work-up, the mixture was concentrated under reduced pressure
  3. customthe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-249089f3299d4371b772d08c5d6877ef
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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