Water → HCID 10369698, compound

HRID 2099153Notes

Reaction equation

HRID 2099153 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([CH3:31])[C:29]=1[CH3:30])[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[C:11]=1[O:25][CH3:26])=[O:8])=[N+:2]=[N-:3].[C:32]([O:36][CH3:37])(=[O:35])[C:33]#[CH:34].O>CC(N(C)C)=O>[CH3:37][O:36][C:32]([C:33]1[N:3]=[N:2][N:1]([C:4]2[CH:5]=[C:6]([C:7](=[O:8])[NH:9][C:10]3[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])[C:11]=3[O:25][CH3:26])[CH:27]=[C:28]([CH3:31])[C:29]=2[CH3:30])[CH:34]=1)=[O:35]

Participants

5

Reactant 3

HCID 962WaterHCID 13536Methyl propiolateHCID 21079201HCID 21079201, compound

Product 1

HCID 10369698HCID 10369698, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 0.112 g (0.252 mmol) of 3-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4,5-dimethyl-benzamide and 0.069 mL (0.756 mmol) of methyl propiolate was stirred in 0.5 mL of DMA at 110° C. overnight. The vial was cooled to room temperature, and the contents were poured into stirring water. The precipitate was collected and chromatographed (10-60% EtOAc in hexanes). Fractions containing predominantly the major product were collected and further purified by precipitating from dichloromethane with hexanes to provide 57 mg of a white powder. The filtrate was combined with the mixed fractions from the first chromatography, and the resulting mixture was chromatographed again to provide 22 mg of the title compound as a pale yellow solid for a total yield of 79 mg (0.149 mmol; 59%), mp: 199° C. ESI MS (m/z 528, 100, M−H).

Workup

  1. additionthe contents were poured
  2. customThe precipitate was collected
  3. customchromatographed (10-60% EtOAc in hexanes)
  4. additionFractions containing predominantly the major product
  5. customwere collected
  6. customfurther purified
  7. customby precipitating from dichloromethane with hexanes

Sources & evidence

ORD record
ord-c96db230f6334a8883af90067eb2f8e5
Source dataset
uspto-grants-2009_08
Patent number
US07569568B2

Reaction notes

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