1,2-Dichloroethane → 7-bromo-1-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline

HRID 221622

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HRID 221622 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][C@@H:14]([CH3:24])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Cl:25][CH2:26][CH2:27]Cl.Cl.ClCC(=N)OCC.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([C@@H:14]([CH3:24])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[C:27]([CH2:26][Cl:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 516892Sodium BicarbonateHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 691054407-bromo-N4-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)quinoline-3,4-diamine

생성물 1

HCID 671574837-bromo-1-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
70 °C

실험 절차

A 1-L, three-necked, Morton flask, equipped with overhead stirrer, was charged with 7-bromo-N4-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)quinoline-3,4-diamine (33.4 g, 81.0 mmol) and 1,2-dichloroethane (400 mL) and the mixture was stirred under N2. Ethyl 2-chloroethanimidoate hydrochloride (29.1 g, 184.0 mmol) was then added in portions and the reaction mixture was heated to 70° C. for 3 days. The reaction mixture was then cooled to ambient temperature and treated with CHCl3 (500 mL) and saturated aqueous NaHCO3 solution (700 mL). The layers were separated and the organic portion was concentrated under reduced pressure to give 38 g of 7-bromo-1-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline as a golden solid.

후처리

  1. temperatureThe reaction mixture was then cooled to ambient temperature
  2. customThe layers were separated
  3. concentrationthe organic portion was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-981adcc57ad14a6dacdb6502098b97d2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207162B2

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