1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile → [1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamine

HRID 578868노트

반응식

HRID 578868 반응식
[Cl:1][C:2]1[C:3]([C:15]2([C:18]#[N:19])[CH2:17][CH2:16]2)=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][CH:9]2[C:11]([F:14])([F:13])[F:12])[CH:7]=1>CO.N.[Ni]>[Cl:1][C:2]1[C:3]([C:15]2([CH2:18][NH2:19])[CH2:17][CH2:16]2)=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][CH:9]2[C:11]([F:14])([F:12])[F:13])[CH:7]=1

참가 물질

5

반응물 1

HCID 895441591-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile

생성물 1

HCID 89544472[1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamine수율 88.2%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 222Ammonia용매HCID 887Methanol용매

실험 절차

509 mg of 1-[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile (step 2) was dissolved in 35 ml of methanol containing 2 ml of ammonia (7N in methanol). The solution was hydrogenated over Raney-nickel (flow: 1 mL/min, 50° C., 40 bar). Then the solvent was removed at reduced pressure to give 455 mg of [1-[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamine as an orange oil. 1H-NMR (CDCl3): 8.30 ppm (s, 1H), 7.87 ppm (s, 1H), 2.94 ppm (s, 2H), 2.33 ppm (m, 1H), 1.85 ppm (m, 1H), 1.78 ppm (s, 2H, broad), 1.46 ppm (m, 1H), 1.22 ppm (m, 1H), 1.00 ppm (m, 2H), 0.90 ppm (m, 2H).

후처리

  1. customThen the solvent was removed at reduced pressure

출처 및 근거

ORD 기록
ord-30732926b0794f3aafd0ceb40839e207
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040708B2

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