Triethylamine → HCID 21090800, compound

HRID 351268Notes

Reaction equation

HRID 351268 reaction equation
[F:1][CH:2]([F:25])[C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[N:5]([C:17]2[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[N:4]=1.CCN(CC)CC.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[CH3:33][S:34]([O:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]([C:17]3[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[N:4]=[C:3]([CH:2]([F:1])[F:25])[CH:7]=2)=[CH:9][CH:10]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21090796HCID 21090796, compound

Product 1

HCID 21090800HCID 21090800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{4-[3-(difluoromethyl)-1-(6-methoxy-3-pyridinyl)-1-H-pyrazol-5-yl]phenyl}ethanol (7.4 g) and Et3N (4.5 ml) in CH2Cl2 (75 ml) was added MsCl (2.5 ml) under ice-cooling. After stirring for 1 hour, the reaction mixture was quenched with water, separated. The aqueous layer was extracted with CH2Cl2 and combined organic layer was washed with water and brine, dried over MgSO4, filtered and evaporated under reduced pressure to give 10.5 g (quant) of 2-{4-[3-(difluoromethyl)-1-(6-methoxy-3-pyridinyl)-1-H-pyrazol-5-yl]phenyl}ethyl methanesulfonate as an oil.

Workup

  1. temperaturecooling
  2. customthe reaction mixture was quenched with water
  3. customseparated
  4. extractionThe aqueous layer was extracted with CH2Cl2 and combined organic layer
  5. washwas washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0bb0929c28e74862a5be04e9de72a32b
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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