Hydrochloric Acid → HCID 18185392, compound

HRID 2186782Notes

Reaction equation

HRID 2186782 reaction equation
NC(C)(C)C[O:4][C:5](=[O:27])[C:6]1[C:11]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][C:9]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[N:8][CH:7]=1.C(Cl)(=O)C(C)(C)C.Cl.[Cl-].[Na+]>O1CCCC1>[C:12]([C:11]1[C:6]([C:5]([OH:27])=[O:4])=[CH:7][N:8]=[C:9]([N:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)[CH:10]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 62493Pivaloyl chlorideHCID 69550554HCID 69550554, compound

Product 1

HCID 18185392HCID 18185392, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1.15 g (2.9 mmol) of 4-benzoyl-6-(4-methyl-piperazin-1-yl)-nicotinic acid 2-amino-2-methyl-propyl ester in 20 ml tetrahydrofuran were added dropwise 367 mg (3.05 mmol) pivaloyl chloride at 0° C. After stirring the light yellow suspension at the same temperature for 1 hour, 1 M aqueous hydrochloric acid was added. Excess pivaloyl chloride was extracted with dichloromethane, the aqueous layer was made alkaline with 28% sodium hydroxide solution and extracted twice with dichloromethane. The organic layer was dried (magnesium sulfate) and evaporated. The residue was dissolved in methanol, 1 M aqueous sodium hydroxide solution was added slowly at 0° C. and the mixture was heated overnight at 65° C. Methanol was evaporated and the aqueous layer was adjusted to pH 5. The solvent was evaporated to yield the product contaminated with sodium chloride, which was used for the next step without further purification.

Workup

  1. extractionExcess pivaloyl chloride was extracted with dichloromethane
  2. extractionextracted twice with dichloromethane
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. customevaporated
  5. dissolutionThe residue was dissolved in methanol
  6. addition1 M aqueous sodium hydroxide solution was added slowly at 0° C.
  7. customMethanol was evaporated
  8. customThe solvent was evaporated
  9. customto yield the product
  10. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-fe6f84a06fa547cdae216a8f61e92fa0
Source dataset
uspto-grants-2002_06
Patent number
US06407111B1

Reaction notes

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