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Cesium carbonate → 5-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2-({1-[2-(trifluoromethyl)benzyl]-1H-1,2,4-triazol-5-yl}sulfonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714724
Notes
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Reaction equation

HRID 714724 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:32])[N:11]([S:13]([C:16]3[N:20]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:31])([F:30])[F:29])[N:19]=[CH:18][N:17]=3)(=[O:15])=[O:14])[N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:40][CH:41]([OH:46])[C:42]([F:45])([F:44])[F:43]>CN(C=O)C.C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:40][CH:41]([OH:46])[C:42]([F:45])([F:44])[F:43])[C:10](=[O:32])[N:11]([S:13]([C:16]3[N:20]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:30])([F:29])[F:31])[N:19]=[CH:18][N:17]=3)(=[O:15])=[O:14])[N:12]=2)=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2206323-Bromo-1,1,1-Trifluoro-2-PropanolHCID 1363853655-(4-Chlorophenyl)-2-({1-[2-(trifluoromethyl)benzyl]-1H-1,2,4-triazol-5-yl}sulfonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 866909365-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-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

2
HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

50 mg (0.10 mmol) of the compound from Example 95A together with 50 mg (0.16 mmol) of cesium carbonate were dissolved in 0.5 ml of DMF, and 30 mg (0.16 mmol) of 3-bromo-1,1,1-trifluoropropan-2-ol were added. The mixture was then stirred at 75° C. for 8 h. For work-up, the reaction mixture was diluted with 0.5 ml of acetonitrile and directly purified chromatographically [Method 19]. This gave 15 mg (22% of theory) of the target compound.

Workup

  1. customdirectly purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-65d93ced5d58406a9f5ea80f05ce9959
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187466B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes