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

HRID 2200398Notes

Reaction equation

HRID 2200398 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-1074a1a6f609496989432d1b8c87a0b6
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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