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

HRID 80535

반응식

HRID 80535 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d71052b2363c431a8a193624a3f04fd1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846664B2

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