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 2039687ノート

反応式

HRID 2039687 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

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].

後処理

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

出典と根拠

ORDレコード
ord-81e3130386c241c88baacb14db14e25c
出典データセット
uspto-grants-2013_11
特許番号
US08580799B2

反応ノート

読み込み中…