Water → HCID 118049791, compound

HRID 595853Notes

Reaction equation

HRID 595853 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C@@H:8]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]2)=[N:6][CH:7]=1.C1C(=O)N([Br:21])C(=O)C1.O>C(#N)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C@@H:8]2[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]2)=[N:6][C:7]=1[Br:21]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 118051208HCID 118051208, compound

Product 1

HCID 118049791HCID 118049791, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Di-tert-butyl (5-((1R,3S)-3-hydroxycyclopentyl)pyrazin-2-yl)carbamate (35 mg, 0.092 mmol) in DCM (461 μl) was added HCl (922 μl, 3.69 mmol), the reaction mixture was stirred at room temperature overnight and concentrated to dryness yielding HCl salt. The crude product was used in next step reaction without purification. LCMS (m/z): 180.1 (MH+), 0.22 min. (+/−)-(1S,3R)-3-(5-aminopyrazin-2-yl)cyclopentanol (15 mg, 0.084 mmol) was dissolved in acetonitrile (2 mL), then NBS (16.39 mg, 0.092 mmol) was added, the reaction mixture was stirred at room temperature for 30 min, water was added, the reaction mixture was then extracted by EtOAc, the organic was dried and concentrated, the crude material was used in next step reaction. LCMS (m/z): 258.1/260.2 (MH+), 0.45 min. Following the above method, using (+/−)-N,N-Di-tert-butyl (5-((1R,3S)-3-hydroxycyclopentyl)pyrazin-2-yl)carbamate, (+/−)-(1R,3R)-3-(5-amino-6-bromopyrazin-2-yl)cyclopentanol was obtained. LCMS (m/z): 258.1/260.1 (MH+), 0.50 min.

Workup

  1. extractionthe reaction mixture was then extracted by EtOAc
  2. customthe organic was dried
  3. concentrationconcentrated
  4. customthe crude material was used in next step reaction
  5. custom258.1/260.2 (MH+), 0.45 min

Sources & evidence

ORD record
ord-b083e2576ed64cb98bf513bb209608a2
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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