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

HRID 332723Notes

Reaction equation

HRID 332723 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:15]([NH2:17])=[O:16])[CH3:14].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]([CH3:14])[C:15]([NH2:17])=[O:16])[CH:5]=[N:4][C:3]=1[C:9]#[N:10]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2775814(2R)-2-Aminopropanamide hydrochlorideHCID 529877443,5-Dichloropyrazine-2-carbonitrile

Product 1

HCID 86685533(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)propanamideYield 100.2%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 3,5-dichloropyrazine-2-carbonitrile (150 mg, 0.862 mmol), D-alaninamide hydrochloride (107 mg, 0.858 mmol) and DIEA (0.400 mL, 2.30 mmol) in NMP (4 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)propanamide as an oil (194 mg).

Workup

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

Sources & evidence

ORD record
ord-c780ed73a5de4cb2b3229cc014f503a9
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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