Sodium Bicarbonate → HCID 131734600, compound

HRID 595863Notes

Reaction equation

HRID 595863 reaction equation
[Br:1][C:2]1[C:3]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[N:4][CH:5]=[C:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:9]2)[N:7]=1.C(=O)(O)[O-].[Na+]>Cl.C1COCC1.CCOC(C)=O.O>[Br:1][C:2]1[C:3]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[N:4][CH:5]=[C:6]([C@@H:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][Si:15]([C:18]([CH3:20])([CH3:21])[CH3:19])([CH3:17])[CH3:16])[CH2:9]2)[N:7]=1

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 131734598HCID 131734598, compound

Product 1

HCID 131734600HCID 131734600, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (+/−)-N-(3-bromo-5-(3-((tert-butyldimethylsilyl)oxy)cyclohexyl)pyrazin-2-yl)pivalamide (97 mg, 0.206 mmol) in 6N HCl (687 μL), THF (687 μL) MeOH (687 μL) was stirred for 2 h. LCMS indicated that the reaction was completed. Solid sodium bicarbonate was added to neutralize the HCl. Dissolved in EtOAc and water. Organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated to provide 72 mg of crude (+/−)-N-(3-bromo-5-((1R,35)-3-((tert-butyldimethylsilyl)oxy)cyclohexyl)pyrazin-2-yl)pivalamide in 98% yield. LCMS (m/z): 358.6 (MH+), 0.70 min.

Workup

  1. customOrganic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b8aaf94263bb46e6a408adb53b0bef2c
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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