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Sodium hydrosulfide → Tert-butyl (6-(3-isopropylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

HRID 219215
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HRID 219215 반응식
[CH3:1][CH:2]([CH3:25])[C:3](=O)[C:4]#[C:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:13][N:14]=2)[N:11]=1.[NH2:26]OS(O)(=O)=O.C(=O)(O)[O-].[Na+].[SH-:37].[Na+]>O.O1CCOCC1>[CH:2]([C:3]1[CH:4]=[C:5]([C:6]2[CH:7]=[CH:8][C:9]3[N:10]([C:12]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:13][N:14]=3)[N:11]=2)[S:37][N:26]=1)([CH3:25])[CH3:1]
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참가 물질

7

반응물 4

HCID 28015Sodium hydrosulfideHCID 76284hydroxylamine-O-sulfonic acidHCID 516892Sodium BicarbonateHCID 57691360Tert-butyl (6-(4-methyl-3-oxopent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

생성물 1

HCID 57691285Tert-butyl (6-(3-isopropylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate수율 22.5%

시약·촉매·용매

2
HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

An aqueous mixture of tert-butyl (6-(4-methyl-3-oxopent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (0.800 g, 2.33 mmol) and hydroxylamine-O-sulfonic acid (0.263 g, 2.33 mol) in water (8.0 mL) and 1,4-dioxane (8.0 mL) was stirred at 0° C. until complete consumption of the organic starting material was observed. The mixture was then carefully treated with solid sodium bicarbonate (0.196 g, 2.33 mmol), followed by treatment with 1.4 M aqueous sodium hydrosulfide (1.83 ml, 2.56 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was diluted with water (20 mL) and extracted with DCM (40 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The concentrated crude material was dissolved in minimal DCM and was purified via MPLC (eluting with 0-10% MeOH/NH4OH in DCM) to yield tert-butyl (6-(3-isopropylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (0.196 g, 22.5% yield) with 82% purity. MS (ESI pos. ion) m/z: 433.0 (M+H). Calc'd Exact Mass for C21H20N8OS: 432.51.

후처리

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionextracted with DCM (40 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationThe concentrated crude material
  7. dissolutionwas dissolved in minimal DCM
  8. customwas purified via MPLC (eluting with 0-10% MeOH/NH4OH in DCM)

출처 및 근거

ORD 기록
ord-979217b073eb4105a405364844328837
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08198448B2

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