1-(2-Phenoxyethyl)piperazine → 5-Chloro-3-nitro-4-[4-(2-phenoxy-ethyl)-piperazin-1-yl]-pyridin-2-ylamine

HRID 416705

반응식

HRID 416705 반응식
[O:1]([CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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:13]2[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:15][CH2:14]2)=[C:22]([N+:23]([O-:25])=[O:24])[C:17]([NH2:16])=[N:18][CH:19]=1

참가 물질

4

반응물 2

HCID 2331871-(2-Phenoxyethyl)piperazineHCID 468676602-Amino-4,5-dichloro-3-nitropyridine

생성물 1

HCID 578972095-Chloro-3-nitro-4-[4-(2-phenoxy-ethyl)-piperazin-1-yl]-pyridin-2-ylamine

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
45 °C

실험 절차

A mixture of 1-(2-phenoxy-ethyl)-piperazine (0.047 g, 0.23 mmol), isopropanol (4.0 ml), and 2-amino-4,5-dichloro-3-nitropyridine (0.034 g, 0.16 mmol) was heated at 45° C. for 18 h. The reaction mixture was allowed to cool to room temperature, absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 10% ethyl acetate in dichloromethane, 20% ethyl acetate in dichloromethane and finally 1% methanol in ethyl acetate/dichloromethane (v/v; 1:4). The title compound was obtained as a yellow solid (0.053 g, 88%); 1H-NMR (500 Mz, DMSO-d6) 2.62 (br s, 4H, piperazine N(CH2)2), 2.76 (t, J=5.62 Hz, 2H, NCH2CH2O), 3.06 (br s, 4H, piperazine N(CH2)2), 4.09 (t, J=5.37 Hz, 2H, NCH2CH2O), 6.95 (m, 5H, 2-NH2 and o-ArH and p-ArH), 7.27 (t, J=11.20 Hz, 2H, m-ArH), 8.06 (s, 1H, 6-H); LC-MS (ESI, m/z) 3.79 min—378, 380 [(M+H)+, Cl isotopic pattern].

후처리

  1. temperatureto cool to room temperature
  2. customabsorbed on silica gel
  3. washwas eluted with 10% ethyl acetate in dichloromethane, 20% ethyl acetate in dichloromethane

출처 및 근거

ORD 기록
ord-9fe8c6f6483f4ef0b14cac26876625bf
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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