Dimethylamine → HCID 10152952, compound

HRID 902242Notes

Reaction equation

HRID 902242 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@H:13]([C:14]([O:16]CC)=[O:15])[C@@H:12]([C:19]3[CH:27]=[CH:26][C:22]4[O:23][CH2:24][O:25][C:21]=4[CH:20]=3)[CH2:11][N:10]2[CH2:28][C:29]([N:31]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:32][CH2:33][CH2:34][CH2:35]Br)=[O:30])=[CH:5][CH:4]=1.[CH3:41][NH:42][CH3:43]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@H:13]([C:14]([OH:16])=[O:15])[C@@H:12]([C:19]3[CH:27]=[CH:26][C:22]4[O:23][CH2:24][O:25][C:21]=4[CH:20]=3)[CH2:11][N:10]2[CH2:28][C:29]([N:31]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:32][CH2:33][CH2:34][CH2:35][N:42]([CH3:43])[CH3:41])=[O:30])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 69275106HCID 69275106, compound

Product 1

HCID 10152952HCID 10152952, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of the compound of Example 547D (0.825 g, 1.34 mmol) in 3 mL of ethanol was added 5 mL of 4.07 M dimethylamine in ethanol; the resultant solution was heated at reflux for 75 min. Solvents were removed in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 9:1 dichloromethane/methanol. The resultant material was taken up in 5 mL of 1.4N NaOH in 5:1 ethanol/water and stirred at ambient temperature for 14 hrs. Solvents were removed in vacuo; the residue was taken up in water, then adjusted to pH 6-7 with 1M HCl (˜7 mL required). The mixture was extracted with EtOAc (3×); the aqueous layer was concentrated in vacuo. The residue was washed 3× with acetonitrile; the combined washes were filtered through Celite and concentrated to give 596 mg of a white foam.

Workup

  1. temperatureat reflux for 75 min
  2. customSolvents were removed in vacuo
  3. customThe residue was purified by flash chromatography on silica gel
  4. washeluting with 9:1 dichloromethane/methanol
  5. customSolvents were removed in vacuo
  6. extractionThe mixture was extracted with EtOAc (3×)
  7. concentrationthe aqueous layer was concentrated in vacuo
  8. washThe residue was washed 3× with acetonitrile
  9. filtrationthe combined washes were filtered through Celite
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1ad2b04dda5b4834819be01badec3a9a
Source dataset
uspto-grants-2008_04
Patent number
US07365093B2

Reaction notes

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