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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
Notes
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Reaction equation

HRID 2039687 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent
HCID 312751,4-DioxaneSolvent

Procedure

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].

Workup

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

Sources & evidence

ORD record
ord-81e3130386c241c88baacb14db14e25c
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580799B2

Reaction notes

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