Diisopropylethylamine → HCID 118046996, compound

HRID 595879Notes

Reaction equation

HRID 595879 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:9][CH2:10][C:11]([OH:13])=O)=[N:6][C:7]=1[Br:8].[CH3:14][N:15](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CN>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:9][CH2:10][C:11]([NH:15][CH3:14])=[O:13])=[N:6][C:7]=1[Br:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6364545Methylamine hydrochlorideHCID 118046715HCID 118046715, compound

Product 1

HCID 118046996HCID 118046996, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-amino-6-bromopyrazin-2-yl)propanoic acid (32 mg, 0.130 mmol) in DMF (1300 μL) was added TBTU (62.6 mg, 0.195 mmol), DIEA (68.1 μL, 0.390 mmol), and methanamine hydrochloride (9.66 mg, 0.143 mmol). The reaction mixture was stirred for 3 h. The reaction mixture was extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude 3-(5-amino-6-bromopyrazin-2-yl)-N-methylpropanamide (74%) was obtained and was used for the next step without further purification. LCMS (m/z): 259/261 (MH+), 0.35 min.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a207e1e79363400ca9ce62f148a4b2b9
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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