Water → (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-(thiophen-2-yl)propanamide

HRID 332796Notes

Reaction equation

HRID 332796 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][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)[C:14]([NH2:16])=[O:15].CCN(C(C)C)C(C)C.O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C@H:13]([CH2:17][C:18]2[S:19][CH:20]=[CH:21][CH:22]=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 86685590(R)-2-amino-3-(thiophen-2-yl)propanamide hydrochloride

Product 1

HCID 86685591(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-(thiophen-2-yl)propanamideYield 76.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,5-dichloropyrazine-2-carbonitrile (137 mg, 0.787 mmol), (R)-2-amino-3-(thiophen-2-yl)propanamide hydrochloride (163 mg, 0.789 mmol) and DIEA (0.350 mL, 2.01 mmol) in DMF (4 mL) was stirred at room temperature for 4 h. Water and EtOAc were added. Organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-(thiophen-2-yl)propanamide (185 mg).

Workup

  1. customOrganic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialwith 5% NaHCO3, dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3c35e02555141abbb157ea9ef6706ff
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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