1,2-Dichloroethane → HCID 49785199、化合物

HRID 1893418ノート

反応式

HRID 1893418 の反応式
[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

参加物

10

反応物 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]pyrazine2 回

生成物 1

HCID 49785199HCID 49785199、化合物収率 10.9%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒3 回HCID 312751,4-Dioxane溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-00945a8fd87644518760808b87b95707
出典データセット
uspto-grants-2013_08
特許番号
US08513248B2

反応ノート

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