N,N-Diethyl-2-propanamine → 5-bromo-N3-(2-chloro-3,6-difluorobenzyl)pyrazine-2,3-diamine

HRID 80535

Reaction equation

HRID 80535 reaction equation
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1.[Cl:10][C:11]1[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:12]=1[CH2:13][NH2:14].C(N(C(C)C)CC)C>CCCCO>[Br:9][C:5]1[N:6]=[C:7]([NH:14][CH2:13][C:12]2[C:15]([F:20])=[CH:16][CH:17]=[C:18]([F:19])[C:11]=2[Cl:10])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 521913N,N-Diethyl-2-propanamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 27735452-Chloro-3,6-difluorobenzylamine

Product 1

HCID 866594195-bromo-N3-(2-chloro-3,6-difluorobenzyl)pyrazine-2,3-diamineYield 70%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-amino-3,5-dibromopyrazine (29 mmol, 7.35 g), 2-chloro-3,6-difluorobenzylamine (29 mmol, 5.16 g), and N, N-diethylisopropylamine (32 mmol, 5.6 mL) in n-BuOH (20 mL) was refluxed for 72 hrs. After volatile components were removed on rotavap, EtOAc and water were added to the residue to facilitate the extraction. The combined organic layers were combined, dried, concentrated, and then subjected to a silica gel column chromatography by using hexanes/EtOAc (4:1) as eluents, furnishing 5-bromo-N3-(2-chloro-3,6-difluorobenzyl)pyrazine-2,3-diamine in 70% yield (7.14 g).

Workup

  1. customAfter volatile components were removed on rotavap
  2. additionEtOAc and water were added to the residue
  3. extractionthe extraction
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d71052b2363c431a8a193624a3f04fd1
Source dataset
uspto-grants-2014_09
Patent number
US08846664B2

Linked notes

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