Hydrochloric Acid → 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol

HRID 1969928Notes

Reaction equation

HRID 1969928 reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][C@H:12]([C:14]2[N:18]3[C:19]4[CH:25]=[CH:24][N:23]([S:26]([C:29]5[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=5)(=[O:28])=[O:27])[C:20]=4[N:21]=[CH:22][C:17]3=[N:16][N:15]=2)[C@H:11]([CH2:36][CH3:37])[CH2:10]1)(C(C)(C)C)(C)C.Cl.CCOC(C)=O>C(O)C.C([C@H]1[C@@H](C2N3C4C=CN(S(C5C=CC(C)=CC=5)(=O)=O)C=4N=CC3=NN=2)C[C@@H](O)C1)C>[CH2:36]([CH:11]1[CH:12]([C:14]2[N:18]3[C:19]4[CH:25]=[CH:24][N:23]([S:26]([C:29]5[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=5)(=[O:28])=[O:27])[C:20]=4[N:21]=[CH:22][C:17]3=[N:16][N:15]=2)[CH2:13][CH:9]([OH:8])[CH2:10]1)[CH3:37]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 67998383HCID 67998383, compound

Product 1

HCID 585575563-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 67999683HCID 67999683, compoundSolvent

Procedure

A scalemic mixture enriched in 1-((1S,2R,4S)-4-(tert-butyldimethylsilyloxy)-2-ethylcyclopentyl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (9.58 g, 17.8 mmol) was dissolved in ethanol (177 mL). Concd HCl (1.75 mL, 21.3 mmol) was added dropwise. After about 1 h, EtOAc (700 mL) was added. The organic mixture was washed with saturated aqueous NaHCO3 (2×120 mL), brine (120 mL), dried over anhydrous MgSO4, filtered and concd under reduced pressure. The residue was purified using silica gel chromatography eluting with 30-100% EtOAc in DCM to give a scalemic mixture enriched in (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol (6.73 g, 89%): LC/MS (Table 1, Method b) Rt=2.11 min; MS m/z: 426 (M+H)+.

Workup

  1. washThe organic mixture was washed with saturated aqueous NaHCO3 (2×120 mL), brine (120 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. customThe residue was purified
  5. washeluting with 30-100% EtOAc in DCM
  6. customto give a scalemic mixture

Sources & evidence

ORD record
ord-1f4a478f8f8a4a3da0b8e7d17b5dc2c6
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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