Hydrochloric Acid → HCID 118045394, compound

HRID 595874Notes

Reaction equation

HRID 595874 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[N:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4]CC1.C(#N)C.Cl.[OH-].[Na+]>C(OCC)(=O)C.O>[NH2:17][C:14]1[N:15]=[CH:16][C:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 118046609HCID 118046609, compound

Product 1

HCID 118045394HCID 118045394, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazin-2-amine (8.68 g, 45.4 mmol) was added acetonitrile (368 mL), water (245 mL) and 3M HCl (76 mL). The reaction was stirred at room temperature for 30 min. The reaction was basified with excess 1M NaOH, and then diluted with of ethyl acetate. The organic layer was separated. The aqueous layer was extracted well with EtOAc/2-methyl THF (1:1) three times. Organic layers were combined and dried over Na2SO4, filtered and concentrated to give 6.91 g of product as free base. LCMS (m/z): 192.12 (MH+), 0.30 min.

Workup

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted well with EtOAc/2-methyl THF (1:1) three times
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d8bd1161d774412ca00940241026c390
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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