Hydrochloric Acid → 2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl)acetamide hydrochloride

HRID 55775

Reaction equation

HRID 55775 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11]([O:13]C1C(F)=C(F)C(F)=C(F)C=1F)=O)[CH2:3]2.N[C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]=[CH:31][CH:30]=[CH:29]2.C(=O)([O-])[O-].Cl.C[N:42](C=O)C>C(#N)C>[ClH:1].[N:2]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[CH:4]([CH2:10][C:11]([NH:42][C:35]1[CH:34]=[C:33]3[C:28]([CH:29]=[CH:30][CH:31]=[N:32]3)=[CH:27][CH:26]=1)=[O:13])[CH2:3]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 113736-AminoquinolineHCID 19660Carbonate IonHCID 86610796Pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

Product 1

HCID 179798312-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl)acetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

90.3 mg (0.24 mmol) of pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride are dissolved in 1 ml of DMF, mixed with 51.6 mg (0.36 mmol) of 6-aminoquinoline and stirred at room temperature overnight. 1 g of MP-carbonate (polymer-bound carbonate, capacity: 2.5-3.5 mmol/g; from Argonaut Technologies, USA) is added. After 1 h, the polystyrene resin is filtered off and washed with THF. The combined filtrates are concentrated in vacuo, and the crude product is purified by preparative HPLC. The hydrochloride is prepared by mixing the product with a mixture of 1 M hydrochloric acid and acetonitrile and concentrating again. Drying under high vacuum results in 44 mg (50.2% of theory) of the title compound.

Workup

  1. waitAfter 1 h
  2. filtrationthe polystyrene resin is filtered off
  3. washwashed with THF
  4. concentrationThe combined filtrates are concentrated in vacuo
  5. customthe crude product is purified by preparative HPLC
  6. customThe hydrochloride is prepared
  7. additionby mixing the product
  8. concentrationconcentrating again
  9. customDrying under high vacuum

Sources & evidence

ORD record
ord-70027d3c3d4d42b3bc9f47f06148eaaa
Source dataset
uspto-grants-2016_09
Patent number
US09433614B2

Linked notes

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