Quinuclidine, 3-amino-, dihydrochloride → HCID 68154736, compound

HRID 1020017Notes

Reaction equation

HRID 1020017 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16]([OH:18])=O)=[CH:10]2)=[CH:5][CH:4]=1.Cl.Cl.[NH2:22][CH:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1.C(CC(CC)([NH-])C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O1CCCC1.CN(C=O)C>[N:25]12[CH2:30][CH2:29][CH:28]([CH2:27][CH2:26]1)[CH:23]([NH:22][C:16]([C:11]1[CH:12]=[CH:13][C:14](=[O:15])[N:9]([C:6]3[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:19])=[CH:8][CH:7]=3)[CH:10]=1)=[O:18])[CH2:24]2

Participants

7

Reactant 4

HCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 61728386HCID 61728386, compoundHCID 131731373HCID 131731373, compound

Product 1

HCID 68154736HCID 68154736, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

After 300 mg (1.18 mmol) of 1-(4-dimethylaminophenyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid was dissolved in 20 mL of tetrahydrofuran and 2 mL of DMF, 391 mg (1.96 mmol) of 3-aminoquinuclidine dihydrochloride and 460 mg (3.54 mmol) of diethyliso-propylamide were added to the solution. After the reaction solution was stirred at room temperature for about 30 minutes, 600 g (1.57 mmol) of 0-(benzotriazole-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) was added to the reaction solution. This reaction solution was stirred at room temperature for about 20 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo, followed by extraction three times with chloroform and an aqueous NaOH solution (pH 12) and purification using liquid chromatography (chloroform:methanol:ammonia water=10:1:0.1) to obtain a target compound (Actual yield: 158 mg, Percent yield: 31%).

Workup

  1. stirringThis reaction solution was stirred at room temperature for about 20 hours
  2. customthe solvent was removed in vacuo
  3. extractionfollowed by extraction three times with chloroform
  4. customan aqueous NaOH solution (pH 12) and purification
  5. customto obtain a target compound (Actual yield: 158 mg, Percent yield: 31%)

Sources & evidence

ORD record
ord-722e36c15b5b4a1b85824cb52303e634
Source dataset
uspto-grants-2014_05
Patent number
US08716309B2

Reaction notes

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