Hydrochloric Acid → HCID 86699302, compound

HRID 331085Notes

Reaction equation

HRID 331085 reaction equation
[Br:1][C:2]1[C:7]2[N:8]=[C:9](SC)[N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=4)=[CH:15][CH:14]=3)[C:6]=2[C:5](=[O:29])[NH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:41][N:42]1[CH2:47][CH2:46][CH:45]([NH2:48])[CH2:44][CH2:43]1.Cl>CN(C=O)C.C(Cl)Cl.CO.O1CCOCC1>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([NH:48][CH:45]3[CH2:46][CH2:47][N:42]([CH3:41])[CH2:43][CH2:44]3)[N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=4)=[CH:15][CH:14]=3)[C:6]=2[C:5](=[O:29])[NH:4][CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 70297m-Chloroperbenzoic acidHCID 27375314-Amino-1-methylpiperidineHCID 86699299HCID 86699299, compound

Product 1

HCID 86699302HCID 86699302, compoundYield 90%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
-10 °C

Procedure

A 40 mL reaction vial was charged with 238e (0.90 g, 1.90 mmol) in 15 mL DMF. The clear solution was cooled to −10° C. To this, was added m-CPBA (1.48 g, 6.00 mmol) at −10° C. The reaction was allowed to warm up to room temperature, and then stirred for additional 30 min at RT. To the mixture was added TEA (0.83 mL, 6.00 mmol) and 1-methylpiperidin-4-amine (685 mg, 6.00 mmol), and then it was stirred at room temperature for 1 hour with monitoring the reaction by LC-MS. The solvent was removed under reduced pressure yielding light brown oily residue. The residue was dissolved in methylene chloride and washed with saturated aqueous sodium bicarbonate solution. The separated organic layer was dried over sodium sulfate, and then concentrated under reduced pressure to yield a solid. The solid was dissolved in a minimum amount of methylene chloride and treated with excess of n-hexanes yielding pale yellow solids. The resulted solids were collected by filtration, rinsed with n-hexanes and then dried in the air yielding a pale yellow solid. The solid was dissolved in the mixture of DCM and methanol. To the clear solution was added 4N HCl in dioxane (12.0 mL), then it was stirred at room temperature for 6 hours. The solvent was removed under reduced pressure yielding the desired product (238, 90% yield).

Workup

  1. customA 40 mL reaction
  2. temperatureto warm up to room temperature
  3. stirringit was stirred at room temperature for 1 hour
  4. customthe reaction by LC-MS
  5. customThe solvent was removed under reduced pressure
  6. customyielding light brown oily residue
  7. washwashed with saturated aqueous sodium bicarbonate solution
  8. dry with materialThe separated organic layer was dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto yield a solid
  11. filtrationThe resulted solids were collected by filtration
  12. washrinsed with n-hexanes
  13. customdried in the air
  14. customyielding a pale yellow solid
  15. stirringit was stirred at room temperature for 6 hours
  16. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2adf2869b7774be68d8660ba6d07ccec
Source dataset
uspto-grants-2014_11
Patent number
US08877763B2

Reaction notes

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