Water → HCID 89507622, compound

HRID 1192823Notes

Reaction equation

HRID 1192823 reaction equation
[H-].[Na+].[OH:3][N:4]=[C:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([NH:8][CH3:9])=[O:7].[CH2:16]([O:20][C:21](=[O:31])[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Cl)[N:24]=1)[CH2:17][C:18]#[CH:19].O>CN(C=O)C.CCOC(C)=O>[CH3:9][NH:8][C:6](=[O:7])[C:5](=[N:4][O:3][CH2:29][C:25]1[N:24]=[C:23]([NH:22][C:21](=[O:31])[O:20][CH2:16][CH2:17][C:18]#[CH:19])[CH:28]=[CH:27][CH:26]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6400952HCID 6400952, compoundHCID 57407594But-3-in-1-yl[6-(chloromethyl)pyridin-2-yl]carbamate

Product 1

HCID 89507622HCID 89507622, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

49 mg (1.22 mmol) of sodium hydride were added to a solution of 200 mg (1.12 mmol) of 2-(hydroxyimino)-N-methyl-2-phenylacetamide (only Z diastereoisomer in 5 ml of DMF, and the suspension was stirred for 30 minutes at room temperature. Then, a solution of 268 mg (1.12 mmol) of but-3-in-1-yl[6-(chloromethyl)pyridin-2-yl]carbamate in 5 ml was added. The mixture was stirred for 3.5 hours at room temperature and then poured into 70 ml of water and admixed with 50 ml of AcOEt. The organic phase was separated off and dried over MgSO4. After removing the solvent, this gave 388 mg (95% purity, 88:12 mixture of Z and E diastereoisomers) of but-3-yn-1-yl{6-[({[2-(methylamino)-2-oxo-1-phenylethylidene]amino}oxy)methyl]pyridin-2-yl}-carbamate.

Workup

  1. stirringThe mixture was stirred for 3.5 hours at room temperature
  2. customThe organic phase was separated off
  3. dry with materialdried over MgSO4
  4. customAfter removing the solvent

Sources & evidence

ORD record
ord-e5a3d009a3c9407686b80dd674ff4d43
Source dataset
uspto-grants-2014_03
Patent number
US08680283B2

Reaction notes

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