N-bromobutanimide → HCID 123354204, compound

HRID 595857Notes

Reaction equation

HRID 595857 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]2[N:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C(=O)N([Br:29])C(=O)C1>C(#N)C>[Br:29][C:17]1[C:18]([NH2:21])=[N:19][CH:20]=[C:15]([CH:11]2[CH2:12][CH2:13][CH2:14][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH2:10]2)[N:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 125487788HCID 125487788, compound

Product 1

HCID 123354204HCID 123354204, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-((1R,3S)-3-((tert-butyldimethylsilyl)oxy)cyclohexyl)pyrazin-2-amine (110 mg, 0.358 mmol) in acetonitrile (5.50 mL) was added NBS (66.9 mg, 0.376 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 min. After quenched with sat sodium thiosulfate and sat NaHCO3, extracted with EtOAc three times. The organic layers were combined and washed with brine, dried over Na2SO4, filtered and concentrated to afford 138 mg of desired cis racemate compound, which was used as it was. LCMS (m/z): 388 (MH+), 0.72 min.

Workup

  1. customAfter quenched with sat sodium thiosulfate
  2. extractionextracted with EtOAc three times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford 138 mg
  8. custom388 (MH+), 0.72 min.

Sources & evidence

ORD record
ord-a1473c1b87e34b2d94695eebde2afe1c
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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