Triethylamine → HCID 21091094, compound

HRID 351239Notes

Reaction equation

HRID 351239 reaction equation
Cl.Cl.[C:3]([C:6]1[CH:10]=[C:9]([C:11]2[CH:20]=[CH:19][C:14]([O:15][CH2:16][CH2:17][NH2:18])=[CH:13][CH:12]=2)[N:8]([C:21]2[CH:22]=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[N:7]=1)([CH3:5])=[CH2:4].CCN(CC)CC.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[C:3]([C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH2:17][NH:18][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:19][CH:20]=2)[N:8]([C:21]2[CH:22]=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[N:7]=1)([CH3:5])=[CH2:4]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 21090819HCID 21090819, compound

Product 1

HCID 21091094HCID 21091094, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-{4-[3-isopropenyl-1-(6-methoxy-3-pyridinyl)-1H-pyrazol-5-yl]phenoxy}ethyl)amine dihydrochloride (126.4 mg) and Et3N (125 μl) in CH2Cl2 (2 ml) was added methanesulfonyl chloride (34.7 μl ) under ice bath cooling. The mixture was stirred at ambient temperature for 1 hour. Additional methanesulfonyl chloride (6.9 μl ) and Et3N (41.6 μl) were added and the reaction mixture was stirred at ambient temperature for 30 minutes. The mixture was concentrated in vacuo, and the residue was partitioned between AcOEt and 1M HCl. The aqueous layer was reextracted with AcOEt. The combined organic layers were washed with saturated aqueous sodiumbicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer silica gel chromatography developed by AcOEt/n-hexane=70%. The seaparated silica gel was extracted with 10% MeOH/CDCl3 and the solvent was evaporated in vacuo. The residue was crystallized from AcOEt-IPE to give N-(2-{4-[3-isopropenyl-1-(6-methoxy-3-pyridinyl)-1H-pyrazol-5-yl]phenoxy}ethyl)methane-sulfonamide (48.0 mg) as white powder.

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at ambient temperature for 30 minutes
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was partitioned between AcOEt and 1M HCl
  5. washThe combined organic layers were washed with saturated aqueous sodiumbicarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative thin layer silica gel chromatography
  9. extractionThe seaparated silica gel was extracted with 10% MeOH/CDCl3
  10. customthe solvent was evaporated in vacuo
  11. customThe residue was crystallized from AcOEt-IPE

Sources & evidence

ORD record
ord-a2c6c00c33a048cfbbe08340f343ebd3
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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