Dimethylcarbamoyl Chloride → HCID 118114513, compound

HRID 1050619Notes

Reaction equation

HRID 1050619 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][NH:10][CH2:9]1)(C)(C)C.CCN(C(C)C)C(C)C.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28]>CN(C=O)C.O>[NH2:7][C@@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:27]([N:26]([CH3:30])[CH3:25])=[O:28])[CH2:9]1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl Chloride2×HCID 81531Diisopropylethylamine2×HCID 54775497tert-Butyl (3R)-azepan-3-ylcarbamate

Product 1

HCID 118114513HCID 118114513, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

(R)-tert-Butyl-azepan-3-ylcarbamate (250 mg, 1.17 mmol) was dissolved in DMF (0.5 mL), and DIEA (0.41 mL, 2.3 mmol). Dimethylcarbamoyl chloride (0.16 mL, 1.8 mmol) was then added and the reaction was stirred at RT for 1 hour. An additional aliquot of dimethylcarbamoyl chloride (0.16 mL, 1.8 mmol), DIEA (0.41 mL, 2.3 mmol), and DMF (0.5 mL) were added and the reaction was stirred for 6 hours. The solution was diluted with water (1 mL) and the solvents were removed under reduced pressure. The residue was dissolved in a mixture of EtOAc and H2O and the aqueous layer was extracted with EtOAc (×2). The organic extracts were combined, washed with brine, dried, and concentrated. The crude material (300 mg) was dissolved in HCl/dioxane (4 M, 2 mL) and stirred at RT for 1 hour. The solid that formed during the reaction was removed by filtration, suspended in EtOAc, and washed with 1 M NaOH (aq). The aqueous solution was then extracted with EtOAc (×3) and the combined organic extracts were washed with brine, dried, and concentrated to give (R)-3-amino-N,N-dimethylazepane-1-carboxamide (508) (˜200 mg crude).

Workup

  1. stirringthe reaction was stirred for 6 hours
  2. customthe solvents were removed under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture of EtOAc and H2O
  4. extractionthe aqueous layer was extracted with EtOAc (×2)
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. dissolutionThe crude material (300 mg) was dissolved in HCl/dioxane (4 M, 2 mL)
  9. stirringstirred at RT for 1 hour
  10. customThe solid that formed during the reaction
  11. customwas removed by filtration
  12. washwashed with 1 M NaOH (aq)
  13. extractionThe aqueous solution was then extracted with EtOAc (×3)
  14. washthe combined organic extracts were washed with brine
  15. customdried
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-34aefe40f60343ddb1da10750f070c35
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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