Pyridine → HCID 85965157, compound

HRID 1678644Notes

Reaction equation

HRID 1678644 reaction equation
ClC1C=CC(N2C([CH:17]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:18]([OH:20])=[O:19])=C3C(CCCC3)=N2)=CC=1.N1C=CC=CC=1.FC(F)(F)C(O[C:38]1[C:43]([F:44])=[C:42]([F:45])[C:41]([F:46])=[C:40]([F:47])[C:39]=1[F:48])=O.C1COCC1.CS(C)=O>CN(C=O)C>[F:44][C:43]1[C:38]([O:20][C:18](=[O:19])[CH2:17][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)=[C:39]([F:48])[C:40]([F:47])=[C:41]([F:46])[C:42]=1[F:45]

Participants

6

Reactant 4

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 21830753dimethylsulfoxide THFHCID 67131112[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid

Product 1

HCID 85965157HCID 85965157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid (4.5 g, 12.1 mmol; example 5.1) in DMF (45 ml) was added pyridine (1.07 ml, 13.3 mmol) and pentafluorophenyl trifluoroacetate (4.16 ml, 24.1 mmol) at ambient temperature under an argon atmosphere. The reaction mixture was stirred at ambient temperature for 12 h, poured onto ice water/0.1 N HCl 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/sat. aqueous NaHCO3 solution 1/1, ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give 2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester as a yellow oil (9 g, 16.7 mmol; quant.) which was directly used in the next reaction step without further purification.

Workup

  1. extractionextracted two times with iPrOAc
  2. washThe combined extracts were washed with ice water/
  3. dry with materialaqueous NaHCO3 solution 1/1, ice water/brine 1/1 and dried over Na2SO4
  4. filtrationAfter filtration the solvent
  5. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-0c7e8b8c48af498fb443c41ad703a76b
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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