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

HRID 2200403Notes

Reaction equation

HRID 2200403 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-ea1d6a3c5d0d4dd0901d8835495b0000
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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