Water → (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-cyclopropylpropanamide

HRID 2200406Notes

Reaction equation

HRID 2200406 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][CH:18]1[CH2:20][CH2:19]1)[C:14]([NH2:16])=[O:15].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]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:14]([NH2:16])=[O:15])[CH:5]=[N:4][C:3]=1[C:9]#[N:10]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 529877443,5-Dichloropyrazine-2-carbonitrileHCID 67509203(R)-2-amino-3-cyclopropylpropanamide hydrochloride

Product 1

HCID 86685539(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-cyclopropylpropanamideYield 99.5%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 3,5-dichloropyrazine-2-carbonitrile (158 mg, 0.908 mmol), (R)-2-amino-3-cyclopropylpropanamide hydrochloride (150 mg, 0.911 mmol) and DIEA (0.400 mL, 2.30 mmol) in NMP (5 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)-3-cyclopropylpropanamide (240 mg).

Workup

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

Sources & evidence

ORD record
ord-6b0090a5ad514bf0809d67de74160f5e
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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