Potassium Cyanide → 3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate

HRID 1969540Notes

Reaction equation

HRID 1969540 reaction equation
[C:1]([O:9][CH:10]1[CH2:14][CH:13]([C:15]2[N:19]3[C:20]4[CH:26]=[CH:25][N:24](S(C5C=CC(C)=CC=5)(=O)=O)[C:21]=4[N:22]=[CH:23][C:18]3=[N:17][N:16]=2)[CH:12]([CH2:37][CH3:38])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[K+]>CO>[C:1]([O:9][CH:10]1[CH2:14][CH:13]([C:15]2[N:19]3[C:20]4[CH:26]=[CH:25][NH:24][C:21]=4[N:22]=[CH:23][C:18]3=[N:17][N:16]=2)[CH:12]([CH2:37][CH3:38])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 585576193-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate

Product 1

HCID 1360092923-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate (5.00 g, 7.84 mmol, prepared from Example #4 Step J using II with benzoic acid, and B) in MeOH (16 mL) was added a solution of potassium cyanide (0.74 mL, 17.2 mmol) in MeOH (16 mL). The reaction was stirred at ambient temperature for about 16 h. The reaction mixture was concd under reduced pressure to afford a residue. The residue was partitioned between water (20 mL) and DCM (20 mL). The layers were separated and the aqueous layer was extracted with DCM (3×10 mL). The extract was then washed with saturated aqueous NaHCO3, dried over anhydrous MgSO4, filtered, and concd under reduced pressure to afford a crude oil. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM to 3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate (2.30 g, 78%) as a red tinted solid. LC/MS (Table 1, Method a) Rt=2.08 min; MS m/z: 376 (M+H)+.

Workup

  1. customto afford a residue
  2. customThe residue was partitioned between water (20 mL) and DCM (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (3×10 mL)
  5. washThe extract was then washed with saturated aqueous NaHCO3
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customconcd under reduced pressure to afford a crude oil
  9. customThe crude material was purified by silica gel chromatography
  10. washeluting with a gradient of 0-10% MeOH in DCM to 3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate (2.30 g, 78%) as a red tinted solid

Sources & evidence

ORD record
ord-4b9ba04c5fa3451cb6da9911fa001e18
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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