Water → (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-4-methylpentanamide

HRID 332716Notes

Reaction equation

HRID 332716 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]([C:18]([NH2:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16].CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C@H:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:18]([NH2:20])=[O:19])[CH:5]=[N:4][C:3]=1[C:9]#[N:10]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 529877443,5-Dichloropyrazine-2-carbonitrileHCID 56776963(R)-2-Amino-4-methylpentanamide hydrochloride

Product 1

HCID 86685528(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-4-methylpentanamideYield 99.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3,5-dichloropyrazine-2-carbonitrile (348 mg, 2.00 mmol), D-leucinamide hydrochloride (333 mg, 2.00 mmol) and DIEA (1.00 mL, 5.75 mmol) in NMP (8 mL) was stirred at room temperature for 20 h. Water and EtOAc were added. Organic phase was separated, dried over Na2SO4, concentrated in vacuo to give (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-4-methylpentanamide as an oil (535 mg).

Workup

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

Sources & evidence

ORD record
ord-0385adcc6f644b019f4da24fcf50a9c5
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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