Butyl iodide → 1-[6-Amino-5-chloro-2-(methoxy)-3-pyridinyl]-3-(1-butyl-4-piperidinyl)-1-propanone

HRID 489795Notes

Reaction equation

HRID 489795 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:19])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:20].I[CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:19])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:20]

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 222625871-(6-Amino-5-chloro-2-methoxy-3-pyridinyl)-3-(4-piperidinyl)-1-propanone

Product 1

HCID 222626001-[6-Amino-5-chloro-2-(methoxy)-3-pyridinyl]-3-(1-butyl-4-piperidinyl)-1-propanoneYield 70.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-(4-piperidinyl)-1-propanone (step 5 in example 9, 110 mg, 0.369 mmol), 1-iodobutane (0.046 ml, 0.406 mmol) and potassium carbonate (102 mg, 0.738 mmol) in tetrahydrofuran (3 ml) was refluxed for 2 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (50 ml), washed with water (5 ml) and brine (10 ml), and dried over potassium carbonate. Removal of solvent gave a pale yellow oil, which was crystallized from methanol to afford 92 mg (64%) of the title compound as a white crystal.

Workup

  1. temperaturewas refluxed for 2 h
  2. washwashed with water (5 ml) and brine (10 ml)
  3. dry with materialdried over potassium carbonate
  4. customRemoval of solvent
  5. customgave a pale yellow oil, which
  6. customwas crystallized from methanol

Sources & evidence

ORD record
ord-5d24181a7f964acfb6a49e4e4eb89419
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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