Pyridine → But-2-yn-1-yl {6-[({[(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylidene]-amino}oxy)methyl]pyridin-2-yl}carbamate

HRID 2039687노트

반응식

HRID 2039687 반응식
[CH3:1][C:2]1[C:3](/[C:7](=[N:14]\[O:15][CH2:16][C:17]2[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=2)/[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][S:5][N:6]=1.N1C=CC=CC=1.[C:30](Cl)(=[O:36])[O:31][CH2:32][C:33]#[C:34][CH3:35]>O1CCOCC1.C(Cl)Cl.O>[CH3:1][C:2]1[C:3]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH:23][C:30](=[O:36])[O:31][CH2:32][C:33]#[C:34][CH3:35])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:4][S:5][N:6]=1

참가 물질

7

반응물 3

HCID 1049PyridineHCID 41316692-Butyn-1-yl chloroformateHCID 873948166-[[(Z)-[(4-methyl-1,2,5-thiadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-amine

생성물 1

HCID 86659838But-2-yn-1-yl {6-[({[(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylidene]-amino}oxy)methyl]pyridin-2-yl}carbamate수율 93%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of 6-[({[(Z)-(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine (100 mg, 0.31 mmol) in dry 1,4-dioxane (5 mL) were added pyridine (37 μL, 0.46 mmol) and but-2-yn-1-yl carbonochloridate (82 mg, 0.62 mmol). The reaction mixture was stirred at room temperature for 18 h, then diluted with DCM (10 mL) and water (10 mL), the organic layer was dried (MgSO4) and concentrated in vacuo. Purification on silica gel afforded but-2-yn-1-yl {6-[({[(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylidene]-amino}oxy)methyl]pyridin-2-yl}carbamate as a colourless oil [120 mg, yield 93%; HPLC/MS: m/z=422 (M+H); log P(HCOOH)=4.28].

후처리

  1. dry with materialthe organic layer was dried (MgSO4)
  2. concentrationconcentrated in vacuo
  3. customPurification on silica gel

출처 및 근거

ORD 기록
ord-81e3130386c241c88baacb14db14e25c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580799B2

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