Triethylamine → HCID 21090840, compound

HRID 351277Notes

Reaction equation

HRID 351277 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([C:28]([N:30]([O:32][CH3:33])[CH3:31])=[O:29])[CH:16]=2)=[CH:11][CH:10]=1.CCN(CC)CC>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([C:28]([N:30]([O:32][CH3:33])[CH3:31])=[O:29])[CH:16]=2)=[CH:13][CH:14]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21090977HCID 21090977, compound

Product 1

HCID 21090840HCID 21090840, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (328 mg) in CH2Cl2 (2 ml) was added to a solution of 5-[4-(2-hydroxyethyl)-phenyl]-N-methoxy-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-3-carboxamide (840 mg) and Et3N (334 mg) in CH2Cl2 (10 ml) under ice bath cooling. The mixture was stirred at same temperature for 1 hour. The mixture was diluted with CHCl3 and washed with 1M HCl, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=80%, 90%. The pure fractions were collected and concentrated in vacuo to give 2-{4-[3-{[methoxy(methyl)amino]carbonyl}-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenyl}ethyl methanesulfonate (1.01 g) as an oil.

Workup

  1. temperaturecooling
  2. washwashed with 1M HCl, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with AcOEt/n-hexane=80%, 90%
  7. customThe pure fractions were collected
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e563baea797a4bbea036fcff1fd3cd24
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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