Water → HCID 58012241, compound

HRID 660956Notes

Reaction equation

HRID 660956 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14]O)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][C:21]([CH3:33])([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH3:22])=[O:19])[N:9]=2)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:40])CC)C.O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][F:40])[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][C:21]([CH3:33])([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:30])[F:32])[CH:24]=3)[CH3:22])=[O:19])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 58011814HCID 58011814, compound

Product 1

HCID 58012241HCID 58012241, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg (0.10 mmol) of 2-[3-(4-chlorophenyl)-4-(2-hydroxyethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide from Example 396 are dissolved in 1.5 ml of dichloromethane and treated at −10° C. with 20.5 μl (0.155 mmol) of diethylaminosulphur trifluoride. This is warmed to RT within 1 hr. Next, the reaction solution is treated with 5 ml of water and extracted twice with 5 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulphate, filtered and concentrated in vacuo. The crude product is purified by preparative HPLC [Method 10]. 37 mg (73% of theory) of the target compound are thus obtained.

Workup

  1. extractionextracted twice with 5 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by preparative HPLC [Method 10]
  6. custom37 mg (73% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-20adf7a0bfe64da29a3552efa1156459
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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