Ethylenediamine → HCID 58007073, compound

HRID 1951903Notes

Reaction equation

HRID 1951903 reaction equation
C(N)CN.O1CCOCC1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C@:18]2([CH3:33])[C@H:22]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([F:30])[CH:24]=3)[NH:21]S(=O)(=O)[NH:19]2)=[CH:14][N:13]=1>C(Cl)(Cl)Cl>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C@@H:22]([NH2:21])[C@:18]([C:15]2[CH:14]=[N:13][C:12]([Cl:11])=[CH:17][CH:16]=2)([NH2:19])[CH3:33])=[CH:24][C:25]=1[F:30]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 312751,4-DioxaneHCID 86660099HCID 86660099, compound

Product 1

HCID 58007073HCID 58007073, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

Ethylenediamine (7.40 ml, 111 mmol) was added to a dioxane (80 ml) solution of the compound (4.15 g, 11.0 mmol) obtained in Step 8 above and the resulting mixture was stirred under heating at 100° C. for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was diluted with chloroform, washed with 1 N aqueous sodium hydroxide solution and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [chloroform:methanol=93:7 (v/v)] to give the title compound (3.35 g, 97%) as a pale yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. washwashed with 1 N aqueous sodium hydroxide solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography [chloroform:methanol=93:7 (v/v)]

Sources & evidence

ORD record
ord-947d716cb11f40099caaa7e8264a4103
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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