Pyridine → [2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester

HRID 889376Notes

Reaction equation

HRID 889376 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:14]([OH:16])=[O:15])=[C:11]3[CH2:23][CH2:24][CH2:25][C:10]3=[N:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.FC(F)(F)C(O[C:37]1[C:42]([F:43])=[C:41]([F:44])[C:40]([F:45])=[C:39]([F:46])[C:38]=1[F:47])=O>CN(C=O)C>[F:43][C:42]1[C:37]([O:15][C:14](=[O:16])[CH:13]([C:12]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=[C:10]3[CH2:25][CH2:24][CH2:23][C:11]=23)[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:38]([F:47])[C:39]([F:46])=[C:40]([F:45])[C:41]=1[F:44]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 67387271[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid

Product 1

HCID 86657983[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid (300 mg, 836 umol) in DMF (3 ml) was added pyridine (70 ul, 920 umol) and pentafluorophenyl trifluoroacetate (290 ul, 1.7 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)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester as an orange oil (762 mg; 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-12fb9eab4b68443bab7d68ef2cac214f
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

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