Triethylamine → Methanesulfonic acid 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethyl ester

HRID 889380Notes

Reaction equation

HRID 889380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:14][OH:15])=[C:11]3[CH2:22][CH2:23][CH2:24][C:10]3=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:32](Cl)([CH3:35])(=[O:34])=[O:33]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:14][O:15][S:32]([CH3:35])(=[O:34])=[O:33])=[C:11]3[CH2:22][CH2:23][CH2:24][C:10]3=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 673874592-(2-(4-Chlorophenyl)-2,4,5,6-tetrahydrocyclopenta[C]pyrazol-3-YL)-2-cyclohexylethanol

Product 1

HCID 86657984Methanesulfonic acid 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethanol (250 mg, 0.72 mmol; example 1.4) in dry dichloromethane (5 ml) was added triethylamine (0.32 ml, 1.19 mmol) at 25° C. Mesyl chloride (0.16 ml, 0.725 mmol) was added dropwise at 0° C. The reaction mixture was allowed to stir at 25° C. for 2 h, diluted with water (5 ml), and the aqueous layer was extracted with dichloromethane (3×10 ml). The combined organic layers were washed sequentially with ice water (10 ml), 10% aqueous NaHCO3 solution (10 ml), brine (10 ml) and finally dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound as light yellow oil (250 mg, 0.58 mmol; 81%), which was sufficiently pure to be used in the next reaction step.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane (3×10 ml)
  2. washThe combined organic layers were washed sequentially with ice water (10 ml), 10% aqueous NaHCO3 solution (10 ml), brine (10 ml)
  3. dry with materialfinally dried over Na2SO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-321531dbdda149edaa7bc1678b0ee5d5
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

Loading…