Methanol → Tert-butyl 3-(2-(2-bromophenylamino)-2-oxoethyl)piperazine-1-carboxylate

HRID 1896104

반응식

HRID 1896104 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:41])[CH2:10][CH:11]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][N:12]1C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O.N1CCNCC1.CO>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:41])[CH2:10][CH:11]1[NH:12][CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:16]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 4837PiperazineHCID 582849301-(9H-fluoren-9-yl)methyl 4-tert-butyl 2-(2-(2-bromophenylamino)-2-oxoethyl)piperazine-1,4-dicarboxylate

생성물 1

HCID 58284918Tert-butyl 3-(2-(2-bromophenylamino)-2-oxoethyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of Example 1A (8.76 g, 14.12 mmol) in dichloromethane (100 mL) was added piperazine (3.65 g, 42.4 mmol). Methanol (50 mL) was added to the solution for solubility, and the resultant mixture was warmed to 40° C. for 14 hours. Once the reaction was complete, purification via flash chromatography (20-100% ethyl acetate/hexanes) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.34 (s, 1 H), 7.83 (d, J=7.12 Hz, 1 H), 7.64 (dd, J=7.97, 1.53 Hz, 1 H), 7.35 (dd, 1 H), 7.08 (dd, 1 H), 3.69-3.85 (m, 2 H), 2.70-2.99 (m, 3 H), 2.53-2.67 (m, 2 H), 2.42 (d, J=6.44 Hz, 2 H), 1.34-1.46 (m, 9 H); MS (APCI+) m/z 400.0 (M+H)+.

후처리

  1. custompurification via flash chromatography (20-100% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-260629b451d9467685a29573265375e0
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518933B2

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