Potassium Carbonate → 4-[3-(6,7-Dimethoxy-3-styryl-quinoxalin-2-ylamino)-propyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1250235노트

반응식

HRID 1250235 반응식
Cl[C:2]1[C:11]([CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:22][CH3:23])=[C:7]([O:20][CH3:21])[CH:8]=2)[N:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37][CH2:38][CH2:39][NH2:40])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCOC(C)=O>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37][CH2:38][CH2:39][NH:40][C:2]2[C:11]([CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][C:9]3[C:4](=[CH:5][C:6]([O:22][CH3:23])=[C:7]([O:20][CH3:21])[CH:8]=3)[N:3]=2)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 22990164tert-Butyl 4-(3-aminopropyl)piperidine-1-carboxylateHCID 734373392-Chloro-6,7-dimethoxy-3-styryl-quinoxaline

생성물 1

HCID 701643374-[3-(6,7-Dimethoxy-3-styryl-quinoxalin-2-ylamino)-propyl]-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture 2-chloro-6,7-dimethoxy-3-styryl-quinoxaline (see Kadin, S. B., Ger Offen., DE 2357186; 255 mg, 0.78 mmol), 4-(3-amino-propyl)-piperidine-1-carboxylic acid tert-butyl ester (see Egbertson, M, U.S. Pat. No. 5494921; 392 mg, 1.6 mmol) and potassium carbonate (220 mg, 1.6 mmol) was heated at 120° C. in DMSO (2 mL) for 17 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc and washed with sat'd aq NaHCO3, sat'd aq NaCl, dried and concentrated under vacuum. The crude residue was chromatographed on SiO2-gel to give 150 mg of a yellow oil. API-MS: 533 (M+1). 1H NMR (300 MHz, CDCl3): d 7.75 (d, 1 H), 7.58 (d, 1 H), 7.35 (m), 7.15 (d, 1 H), 4.05 (m), 3.99 (s, 3 H), 3.97 (s, 3 H), 3.54 (bs, 1 H), 2.68 (t, 2 H),1.75 (m), 1.42 (s, 9 H), 1.1 (m).

후처리

  1. washwashed with sat'd aq NaHCO3
  2. customdried
  3. concentrationconcentrated under vacuum
  4. customThe crude residue was chromatographed on SiO2-gel

출처 및 근거

ORD 기록
ord-31ce23313443412a9c9bad6cbbe15daf
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06337332B1

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