Hydrochloric Acid → HCID 136009417, compound

HRID 1969809Notes

Reaction equation

HRID 1969809 reaction equation
[CH2:1]([CH:3]1[CH2:7][CH:6]([O:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:5][CH:4]1[C:15]1[N:19]2[C:20]3[CH:26]=[CH:25][N:24](S(C4C=CC(C)=CC=4)(=O)=O)[C:21]=3[N:22]=[CH:23][C:18]2=[N:17][N:16]=1)[CH3:2].[OH-].[Na+].Cl>O1CCOCC1>[CH2:1]([C@@H:3]1[CH2:7][C@H:6]([O:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:5][C@@H:4]1[C:15]1[N:19]2[C:20]3[CH:26]=[CH:25][NH:24][C:21]=3[N:22]=[CH:23][C:18]2=[N:17][N:16]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58557381HCID 58557381, compound

Product 1

HCID 136009417HCID 136009417, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 1-(2-ethyl-4-(tetrahydro-2H-pyran-4-yloxy)cyclopentyl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.145 g, 0.285 mmol) in p-dioxane (6.00 mL) was added an aqueous solution of NaOH (1 N, 1.50 mL, 1.50 mmol). The reaction mixture was stirred at about 55° C. for about 45 min, then cooled to ambient temperature. The reaction mixture was acidified to about pH 2 by the addition of aqueous HCl (1 N, 6 mL). The aqueous layer was extracted with DCM (3×20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concd to give a brown residue. The crude material was purified by silica gel chromatography using a gradient of 1-10% MeOH in DCM. The stereoisomers were separated using AA (Table 2, Method 32, Rt=15.5 min, or =negative) to give 1-((1S,2R,4S)-2-ethyl-4-(tetrahydro-2H-pyran-4-yloxy)cyclopentyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.048 g, 48%): LC/MS (Table 1, Method a) Rt=1.70 min; MS m/z: 356 (M+H)+.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionThe aqueous layer was extracted with DCM (3×20 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customto give a brown residue
  6. customThe crude material was purified by silica gel chromatography
  7. customThe stereoisomers were separated

Sources & evidence

ORD record
ord-14e155d6f17d4d8a9447416e26520598
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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