Hydrochloric Acid → HCID 59263079, compound

HRID 643723Notes

Reaction equation

HRID 643723 reaction equation
[CH:1]([C@@:4]1([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:8][C@H:7](N)[CH:6]=[CH:5]1)([CH3:3])[CH3:2].C1(=O)C=CC=CC1=[O:34].Cl.[OH-].[Na+]>CO.O.O1CCCC1>[CH:1]([C@:4]1([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:5][CH2:6][C:7](=[O:34])[CH2:8]1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 114211,2-BenzoquinoneHCID 14798Sodium HydroxideHCID 68484653(1S,4S)-4-isopropyl-4-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopent-2-en-1-amine

Product 1

HCID 59263079HCID 59263079, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1S,4S)-4-isopropyl-4-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopent-2-en-1-amine (3.5 g, 9.2 mmol) and 3,5-Cyclohexadiene-1,2-dione, 3,5-bis(1,1-dimethylethyl)-(2.20 g, 9.99 mmol) in Methanol (85 mL) was stirred at room temperature for 30 minutes. Tetrahydrofuran (85 mL) and 1N HCl (10 mL) were added and the resulting mixture was stirred overnight at room temperature. The mixture was diluted with water and the organics evaporated. The remaining aqueous was made basic with 1N NaOH and extracted with EtOAc three times. The combined extracts were dried (Magnesium sulfate), filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (1:1 EtOAc/Hexanes) to yield (3.16 g, 90%) of the title compound. MS calculated for C19H22F3N3O2: (M+H) 382; found 382.1. Step B:

Workup

  1. extractionextracted with EtOAc three times
  2. dry with materialThe combined extracts were dried (Magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography (1:1 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-4cf2888ea6da4c74b501843cee6e0c70
Source dataset
uspto-grants-2010_04
Patent number
US07700624B2

Reaction notes

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