4-Azaindole → HCID 58387973, compound

HRID 2080229Notes

Reaction equation

HRID 2080229 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:19]=CC3C(=CC=CC=3)N=2)=[O:9])=[CH:4][CH:3]=1.N1[C:30]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1.Cl.Cl[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[N:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:19]=[C:30]3[C:25](=[CH:24][CH:23]=2)[N:26]=[CH:27][CH:28]=[CH:29]3)=[O:9])=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 92264-AzaindoleHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 67119603HCID 67119603, compound

Product 1

HCID 58387973HCID 58387973, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of quinoline carboxylic acid 4-hydroxybenzylamide described in Preparation Example E+-1 (20 mg, 0.0719 mmol) and 2-chloromethyl-pyridine hydrochloride (12 mg, 0.0719 mmol) in N,N-dimethyl formamide (1.0 mL) was added potassium carbonate (298 mg, 2.16 mmol), and the solution was stirred at room temperature for 12 hours. Ethyl acetate and water were added to the reaction solution, which was then partitioned, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound was obtained.

Workup

  1. customwas then partitioned
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound
  5. customwas obtained

Sources & evidence

ORD record
ord-f267d357858945c6820d8fb8fa75eccd
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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