Ethylamine → HCID 22386202, compound

HRID 895283Notes

Reaction equation

HRID 895283 reaction equation
[CH2:1]([NH2:3])[CH3:2].[Cl:4][C:5]1[C:6]([C:15]([N:17]([CH:26]([C:30]2[CH:39]=[CH:38][C:33]3[O:34][CH2:35][CH2:36][O:37][C:32]=3[CH:31]=2)[C:27]([NH2:29])=[O:28])[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[O:16])=[N:7][C:8](S(C)(=O)=O)=[N:9][CH:10]=1>C1COCC1>[Cl:4][C:5]1[C:6]([C:15]([N:17]([CH:26]([C:30]2[CH:39]=[CH:38][C:33]3[O:34][CH2:35][CH2:36][O:37][C:32]=3[CH:31]=2)[C:27]([NH2:29])=[O:28])[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[O:16])=[N:7][C:8]([NH:3][CH2:1][CH3:2])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 22386200HCID 22386200, compound

Product 1

HCID 22386202HCID 22386202, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylamine was passed through an ice-cold solution of the sulfone from example 243 (0.15 g, 0.28 mmol) in THF (3 ml) for 20 minutes. After 2 hours at room temperature, the solvent was evaporated. The residue was dissolved in ethyl acetate (10 ml) and the solution was washed with water (10 m[), saturated NaHCO3 solution (2×10 ml), brine (10 ml), dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (10 g) eluting with a gradient of pentane-ethyl acetate from 90110 to 30/70 in 10% increments of ethyl acetate to give the title compound as a foam 107 mg, (76%).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate (10 ml)
  3. washthe solution was washed with water (10 m[), saturated NaHCO3 solution (2×10 ml), brine (10 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (10 g)
  8. washeluting with a gradient of pentane-ethyl acetate from 90110 to 30/70 in 10% increments of ethyl acetate

Sources & evidence

ORD record
ord-d6d0be33d149414b80fc1804da85b300
Source dataset
uspto-grants-2005_07
Patent number
US06914160B1

Reaction notes

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