Water → (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)butanamide

HRID 332780

Reaction equation

HRID 332780 reaction equation
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](Cl)[N:7]=1.Cl.[NH2:12][C@H:13]([CH2:17][CH3:18])[C:14]([NH2:16])=[O:15].CCN(C(C)C)C(C)C.O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C@H:13]([CH2:17][CH3:18])[C:14]([NH2:16])=[O:15])[CH:5]=[N:4][C:3]=1[C:9]#[N:10]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 16218339(2R)-2-aminobutanamide hydrochlorideHCID 529877443,5-Dichloropyrazine-2-carbonitrile

Product 1

HCID 86685581(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)butanamideYield 97.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,5-dichloropyrazine-2-carbonitrile (628 mg, 3.60 mmol), 2-(R)-amino-butanamide hydrochloride (500 mg, 3.60 mmol) and DIEA (1.60 mL, 9.20 mmol) in DMF (10 mL) was stirred at room temperature for 4 h. Water and EtOAc were added. Organic phase was separated, washed with water, dried over Na2SO4, concentrated in vacuo to give (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)butanamide (843 mg) as a semi-solid.

Workup

  1. customOrganic phase was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd36a7092b1d48e18c4bdfd4b9d3af91
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Linked notes

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