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

HRID 2200391Notes

Reaction equation

HRID 2200391 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-d490c670f2454797a7e4323b74aeb677
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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