Hydrochloric Acid → 8,9,10,11-Tetrahydropyrazino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride

HRID 1364032노트

반응식

HRID 1364032 반응식
[ClH:1].[NH2:2][C:3]1[C:12]2[N:13]=[C:14]3[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16][N:15]3[C:11]=2[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1>O1CCOCC1.ClCCl>[ClH:1].[CH:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:11]1[N:15]3[CH2:16][CH2:17][NH:18][CH2:19][C:14]3=[N:13][C:12]=1[C:3]([NH2:2])=[N:4]2

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 58923896tert-butyl 6-amino-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

생성물 1

HCID 669586758,9,10,11-Tetrahydropyrazino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

Hydrogen chloride (300 mL of a 4 N solution in 1,4-dioxane) was added to a solution of tert-butyl 6-amino-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate (34.74 g, 102.36 mmol) in dichloromethane (300 mL). The reaction was stirred overnight at ambient temperature and then concentrated under reduced pressure. The resulting solid was suspended in dichloromethane, isolated by filtration, and washed sequentially with dichloromethane, diethyl ether, hexane, and diethyl ether. The solid was then triturated with methanol and isolated by filtration to provide 11.58 g of 8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride as a white solid. The filtrate was concentrated under reduced pressure, dissolved in water, and precipitated with 1,4-dioxane to provide an additional 6.95 g of product.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customisolated by filtration
  3. washwashed sequentially with dichloromethane, diethyl ether, hexane, and diethyl ether
  4. customThe solid was then triturated with methanol
  5. customisolated by filtration

출처 및 근거

ORD 기록
ord-576ce7cd1a7a4faaa226395ec87ddb73
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888349B2

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