1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66899251, 화합물

HRID 19350노트

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HRID 19350 반응식
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH2:9][N:8]([CH:10]([CH2:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:11]([OH:13])=O)[C:7](=[O:20])[CH:6]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH3:46][C:47]1([CH3:59])[O:51][C@H:50]([CH2:52][N:53]2[CH:57]=[CH:56][C:55]([NH2:58])=[N:54]2)[CH2:49][O:48]1>ClCCl>[CH3:46][C:47]1([CH3:59])[O:51][C@H:50]([CH2:52][N:53]2[CH:57]=[CH:56][C:55]([NH:58][C:11](=[O:13])[CH:10]([N:8]3[CH2:9][C:5]([O:4][C:3]4[CH:21]=[CH:22][CH:23]=[CH:24][C:2]=4[Cl:1])=[CH:6][C:7]3=[O:20])[CH2:14][CH2:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[N:54]2)[CH2:49][O:48]1

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59344941(R)-1-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amineHCID 668953032-[4-(2-Chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5-dimethyl-hexanoic acid

생성물 1

HCID 66899251HCID 66899251, 화합물수율 29%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
25 °C

실험 절차

In a round bottom flask under argon was placed 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5-dimethyl-hexanoic acid (32 mg, 0.091 mmol) in dichloromethane (3 mL). To this mixture was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (20 μL, 0.10 mmol) and 1-hydoxybenzotriazole (13 mg, 0.096 mmol) and stirred at 25° C. for 2 h. After this time period, 1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-ylamine (prepared as in Example 49, 21 mg, 0.109 mmol) was added and stirred for 16 h at 25° C. After this time, the mixture was diluted with dichloromethane (10 mL) and washed with a 1N aqueous hydrochloric acid solution (10 mL), water (10 mL) and a saturated aqueous sodium bicarbonate solution (10 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by AnaLogix IntelliFlash flash chromatography (4 g column, 30% ethyl acetate/hexanes to 100% ethyl acetate/hexanes) afforded 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5-dimethyl-hexanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-amide (14 mg, 29%) as a colorless oil.

후처리

  1. customIn a round bottom flask under argon was placed
  2. stirringstirred for 16 h at 25° C
  3. washwashed with a 1N aqueous hydrochloric acid solution (10 mL), water (10 mL)
  4. dry with materiala saturated aqueous sodium bicarbonate solution (10 mL), dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by AnaLogix IntelliFlash flash chromatography (4 g column, 30% ethyl acetate/hexanes to 100% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-bedd9d690b5940938fd6adf98919bae8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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