N-(2-aminoethyl)acetamide → HCID 59191335, compound

HRID 1023965Notes

Reaction equation

HRID 1023965 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH2:7])(=[O:3])[CH3:2].[CH2:8]([C:10]1[CH:27]=[CH:26][C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][C:16]=2[F:25])=[C:12]([O:28][CH3:29])[CH:11]=1)[CH3:9]>C1COCC1>[CH2:8]([C:10]1[CH:27]=[CH:26][C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])(=[O:23])=[O:22])=[CH:17][C:16]=2[F:25])=[C:12]([O:28][CH3:29])[CH:11]=1)[CH3:9]

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 59191302HCID 59191302, compound

Product 1

HCID 59191335HCID 59191335, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Acetylethylenediamine (1.1 mmol; 0.10 mL) was slowly added to a solution of 4-(4-ethyl-2-methoxyphenoxy)-3-fluorobenzenesulfonyl chloride (0.94 mmol; 325 mg) and TEA (2.8 mmol; 0.40 mL) in anhydrous THF (5 mL), under argon at 0° C. The reaction was stirred overnight with progressive warming to room temperature. Concentrated, the mixture was purified by chromatography (dichloromethane/methanol/ammonia gradient) to yield the title compound as a yellow oil (142 mg; 0.35 mmol; 37%) used as such in the following reaction.

Workup

  1. concentrationConcentrated
  2. customthe mixture was purified by chromatography (dichloromethane/methanol/ammonia gradient)

Sources & evidence

ORD record
ord-79137e9604a74ac49a752387d1663f6b
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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