Triethylamine → HCID 88585370, compound

HRID 2206899Notes

Reaction equation

HRID 2206899 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:30])([F:29])[F:28])[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[C:18]([CH2:25]O)=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].C([N:33](CC)CC)C.CS(Cl)(=O)=O.O.N>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:30])([F:29])[F:28])[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[C:18]([CH2:25][NH2:33])=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12896473Azane;hydrateHCID 88585369HCID 88585369, compound

Product 1

HCID 88585370HCID 88585370, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

{6-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-(trifluoromethyl)pyridin-3-yl}methanol (Reference document: WO2010/043315) (1.8 g) and triethylamine (0.5 g) were dissolved in acetonitrile (30 mL), and an acetonitrile (10 mL) solution of methanesulfonyl chloride (0.5 g) was added dropwise thereto under ice cooling. Upon the completion of the dropwise addition, the reaction solution was stirred at room temperature for 1 hour, and then the resulting solution was added dropwise to a mixture solution containing 28% ammonia water (50 mL) and acetonitrile (200 mL), which had been prepared separately, under ice cooling. After stirring at room temperature for 12 hours, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The solvent was distilled off and the purification was carried out by silica gel chromatography to obtain the title compound (1.25 g).

Workup

  1. additionUpon the completion of the dropwise addition
  2. additionthe resulting solution was added dropwise to a mixture solution
  3. customhad been prepared separately, under ice cooling
  4. stirringAfter stirring at room temperature for 12 hours
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe purification

Sources & evidence

ORD record
ord-170c354edca04d039a90047107bccd2c
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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