Hydrochloric Acid → HCID 59336110, compound

HRID 2046360Notes

Reaction equation

HRID 2046360 reaction equation
Cl.[CH:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([N:15]([CH3:36])[C:16](=[O:35])[CH2:17][O:18][C:19]3[N:24]=[C:23]([CH3:25])[C:22]([NH:26]C(=O)OC(C)(C)C)=[C:21]([CH3:34])[N:20]=3)[CH2:11][CH2:10]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+]>C(Cl)(Cl)Cl>[NH2:26][C:22]1[C:23]([CH3:25])=[N:24][C:19]([O:18][CH2:17][C:16]([N:15]([CH:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)[CH2:10][CH2:11]2)[CH3:36])=[O:35])=[N:20][C:21]=1[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59336176Tert-butyl 2-(2-((1-(cyclohexylmethyl)piperidine-4-yl)(methyl)amino)-2-oxoethoxy)-4,6-dimethylpyrimidine-5-ylcarbamate

Product 1

HCID 59336110HCID 59336110, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6N HCl (0.7 mL) was added to a chloroform (0.5 mL) solution of Compound 32 (39 mg) and the mixture was stirred at room temperature for 1 hour. While the reaction mixture was cooled with ice, a 4N aqueous sodium hydroxide solution was added to neutralize the mixture. The resulting product was extracted with chloroform and the organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd., NH-DM1020) column chromatography (ethyl acetate) to give 23 mg (76% yield) of the title compound.

Workup

  1. temperatureWhile the reaction mixture was cooled with ice
  2. extractionThe resulting product was extracted with chloroform
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd., NH-DM1020) column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-77650a83b32540639fab1e9c5c98be17
Source dataset
uspto-grants-2013_11
Patent number
US08592435B2

Reaction notes

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