Diisopropylethylamine → 5-Chloro-4-(4-(4-chlorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine

HRID 63588

반응식

HRID 63588 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([Cl:12])=[CH:4][N:3]=1.[Cl:13][C:14]1[CH:26]=[CH:25][C:17]([CH2:18][N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[Cl:12][C:5]1[C:6]([N:22]2[CH2:21][CH2:20][N:19]([CH2:18][C:17]3[CH:25]=[CH:26][C:14]([Cl:13])=[CH:15][CH:16]=3)[CH2:24][CH2:23]2)=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH2:1])=[N:3][CH:4]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 1348264-ChlorobenzylpiperazineHCID 468676602-Amino-4,5-dichloro-3-nitropyridine

생성물 1

HCID 578972545-Chloro-4-(4-(4-chlorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine

시약·촉매·용매 1

HCID 3776Isopropanol용매2회

반응 조건

온도
45 °C

실험 절차

To a mixture of 2-amino-4,5-dichloro-3-nitropyridine (0.152 g, 0.73 mmol) and isopropanol (22 mL) was added 1-(4-chlorobenzyl)piperazine (0.165 g, 0.78 mmol) followed by diisopropylethylamine (0.17 mL, 0.97 mmol). The reaction mixture was heated at 45° C. for 18 h, then allowed to cool to room temperature, and diluted with isopropanol (5 mL). The precipitate was collected by filtration, washed with isopropanol and diethyl ether. The title compound was thus obtained as a yellow solid (0.215 g, 77%); 1H-NMR (500 MHz, DMSO-d6) 2.48 (br s, obscured by DMSO peak, 4H, piperazine C—H), 3.06 (br t, J=4.3 Hz, 4H, piperazine C—H), 3.52 (s, 2H, NCH2C6H4Cl), 6.95 (s, 2H, NH2), 7.35 (d, J=8.5 Hz, 2H) and 7.38 (d, J=8.5 Hz, 2H) (3,5-ArH and 2,6-ArH), 8.06 (s, 1H, 6-H); LC-MS (ESI, m/z): Rt=1.70 min-382, 384, 386 [(M+H)+, Cl2 isotopic pattern].

후처리

  1. temperatureto cool to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with isopropanol and diethyl ether

출처 및 근거

ORD 기록
ord-b74670b74f544214bff977bf5846c935
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447092B2

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