1,2-Dichloroethane → HCID 49785199, 화합물

HRID 1893418노트

반응식

HRID 1893418 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([OH:6])=O.C(Cl)CCl.ON1C2C=CC=CC=2N=N1.[C:27]1([C:33]2[N:37]3[CH2:38][CH2:39][NH:40][CH2:41][C:36]3=[N:35][CH:34]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(C(C)C)CC)(C)C.Cl>ClCCl.O1CCOCC1.C(OCC)C>[ClH:1].[C:27]1([C:33]2[N:37]3[CH2:38][CH2:39][N:40]([C:4]([C:3]4[C:7]([Cl:12])=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=4[Cl:1])=[O:6])[CH2:41][C:36]3=[N:35][CH:34]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

10

반응물 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 57642,4,6-Trichlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 248204983-Phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine2회

생성물 1

HCID 49785199HCID 49785199, 화합물수율 10.9%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매3회HCID 312751,4-Dioxane용매

실험 절차

2,4,6-Trichlorobenzoic acid (0.169 g, 0.750 mmol), EDC (0.144 g, 0.750 mmol) and 1-hydroxybenztriazole (0.115 g, 0.750 mmol) were stirred in dichloromethane (DCM) (5 mL) for 15 minutes. 3-Phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (100 mg, 0.5 mmol, Intermediate 3) and diisopropylethylamine (0.175 mL, 1.000 mmol) were added and the solution stirred at room temperature for 16 hr. The mixture was diluted with DCM (50 ml) and washed with saturated sodium bicarbonate (25 ml), water (3×25 ml), brine, dried over anhydrous sodium sulfate and concentrated to a crude oil. The crude oil was twice purified by mass-directed automated preparative HPLC to afford an oil. The purified product was dissolved in dichloromethane (3 ml) and treated with 4N HCl in dioxane (500 uL). The solvents were removed in vacuo and the solid tritruated with diethyl ether to afford product 3-phenyl-7-[(2,4,6-trichlorophenyl)carbonyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine hydrochloride (0.018 g, 0.041 mmol, 8.12% yield)

후처리

  1. washwashed with saturated sodium bicarbonate (25 ml), water (3×25 ml), brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated to a crude oil
  4. customThe crude oil was twice purified
  5. customto afford an oil
  6. customThe solvents were removed in vacuo

출처 및 근거

ORD 기록
ord-00945a8fd87644518760808b87b95707
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513248B2

반응 노트

불러오는 중…