1-((2-Chloro-6-fluorophenyl)methyl)piperazine → 5-Chloro-4-(4-(2-chloro-6-fluorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine

HRID 416713

반응식

HRID 416713 반응식
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[NH2:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[C:21](Cl)[C:20]([Cl:27])=[CH:19][N:18]=1>C(O)(C)C>[Cl:27][C:20]1[C:21]([N:8]2[CH2:7][CH2:6][N:5]([CH2:4][C:3]3[C:11]([F:15])=[CH:12][CH:13]=[CH:14][C:2]=3[Cl:1])[CH2:10][CH2:9]2)=[C:22]([N+:23]([O-:25])=[O:24])[C:17]([NH2:16])=[N:18][CH:19]=1

참가 물질

4

반응물 2

HCID 7357371-((2-Chloro-6-fluorophenyl)methyl)piperazineHCID 468676602-Amino-4,5-dichloro-3-nitropyridine

생성물 1

HCID 578972505-Chloro-4-(4-(2-chloro-6-fluorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
45 °C

실험 절차

A mixture of 1-(2-chloro-6-fluorobenzyl)piperazine (0.063 g, 0.28 mmol), isopropanol (4.3 ml), and 2-amino-4,5-dichloro-3-nitropyridine (0.042 g, 0.20 mmol) was heated at 45° C. for 22 h. The reaction mixture was allowed to cool to room temperature, and concentrated in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted first with 30% petroleum ether 60-80° C., and then ethyl acetate. The title compound was obtained as a yellow solid (0.050 g, 62%); 1H-NMR (500 Mz, DMSO-d6) 2.56 (br s, 4H, piperazine N(CH2)2), 3.01 (br s, 4H, piperazine N(CH2)2), 3.66 (s, 2H, NCH2), 6.94 (s, 2H, 2-NH2), 7.23 (t, J=8.91 Hz, 1H) and 7.38 (m, 2H) (ArH), 8.06 (s, 1H, 6-H); LC-MS (ESI, m/z) 4.85 min—400, 402, 404 [(M+H)+, Cl2 isotopic pattern].

후처리

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was absorbed on silica gel
  4. washwas eluted first with 30% petroleum ether 60-80° C.

출처 및 근거

ORD 기록
ord-fe4819e48d10437488fe34d25a56f14f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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