Water → 2-(6-Chloro-5-cyanopyrazin-2-ylamino)-4,4,4-trifluorobutanamide

HRID 332728Notes

Reaction equation

HRID 332728 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][CH:13]([CH2:17][C:18]([F:21])([F:20])[F:19])[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][CH:13]([CH2:17][C:18]([F:21])([F:20])[F:19])[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 866661692-Amino-4,4,4-trifluorobutanamide hydrochloride

Product 1

HCID 866855372-(6-Chloro-5-cyanopyrazin-2-ylamino)-4,4,4-trifluorobutanamideYield 88.1%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 3,5-dichloropyrazine-2-carbonitrile (50 mg, 0.287 mmol), 2-amino-4,4,4-trifluorobutanamide hydrochloride (50 mg, 0.259 mmol) and DIEA (0.150 mL, 0.862 mmol) in NMP (1 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 2-(6-chloro-5-cyanopyrazin-2-ylamino)-4,4,4-trifluorobutanamide (67 mg).

Workup

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

Sources & evidence

ORD record
ord-196c513330d04250bd0fe2c369146593
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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