Triethylamine → HCID 87281404, compound

HRID 1678692Notes

Reaction equation

HRID 1678692 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:18][OH:19])=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1.CCN(CC)CC.[S:33](Cl)([CH3:36])(=[O:35])=[O:34]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:18][O:19][S:33]([CH3:36])(=[O:35])=[O:34])=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67131043HCID 67131043, compound

Product 1

HCID 87281404HCID 87281404, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [rac]-2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-ethanol (example 37.1) (400 mg, 1.1 mmol) in dry DCM (15 ml) was added Et3N (0.64 ml, 3.32 mmol) at room temperature. Mesyl chloride (0.16 ml, 2.22 mmol) was then added to this reaction mixture dropwise at 0° C.; and the reaction mixture was stirred at room temperature for 2 hours. TLC shows complete consumption of [rac]-2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-ethanol. The reaction mixture was diluted with H2O (10 ml) and the aqueous layer was extracted with DCM (3×10 ml). Combined organic layers were washed with ice water (10 ml), 10% NaHCO3 (10 ml), brine (10 ml) and finally dried over Na2SO4. Organic layer was distilled under reduced pressure to get light yellow oil (500 mg), which was purified by column chromatography [SiO2 (230-400 mesh), EtOAc:Hexane 10/90] to give the title compound (370 mg, 76%) as a light yellow liquid.

Workup

  1. customconsumption of [rac]-2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-ethanol
  2. additionThe reaction mixture was diluted with H2O (10 ml)
  3. extractionthe aqueous layer was extracted with DCM (3×10 ml)
  4. washCombined organic layers were washed with ice water (10 ml), 10% NaHCO3 (10 ml), brine (10 ml)
  5. dry with materialfinally dried over Na2SO4
  6. distillationOrganic layer was distilled under reduced pressure

Sources & evidence

ORD record
ord-9ddbc3a1850b4d8d97b855cdbe80a5fe
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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