Ammonium Chloride → HCID 59409534, compound

HRID 659952Notes

Reaction equation

HRID 659952 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][C:5](Cl)=[O:6].[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:20]3=[N:21][CH:22]=[C:23]([CH3:25])[CH:24]=[C:19]3[NH:18][C:17]=2[C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH2:32])[CH:27]=2)=[CH:12][CH:11]=1.[Cl-].[NH4+]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:8])[CH2:4][C:5]([NH:32][C:28]1[CH:27]=[C:26]([C:17]2[NH:18][C:19]3[C:20](=[N:21][CH:22]=[C:23]([CH3:25])[CH:24]=3)[C:16]=2[C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)[CH:31]=[CH:30][N:29]=1)=[O:6]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 123460Methyl malonyl chloride2×HCID 59409536HCID 59409536, compound

Product 1

HCID 59409534HCID 59409534, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Chlorocarbonyl-acetic acid methyl ester (129 mg, 0.9 mmole) is added to a solution of 200 mg (0.62 mmole) of 4-[3-(4-Fluoro-phenyl)-6-methyl-1H-pyrrolo[3,2-b]pyridin-2-yl]-pyridin-2-ylamine (prepared following the procedure for example 7) in 3 mL of pyridine at room temperature. After 30 hours at room temperature, Chlorocarbonyl-acetic acid methyl ester (129 mg, 0.9 mmole) is added again to the reaction mixture stirred 12 more hours at room temperature. The reaction mixture is then poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. After concentration the solid residue is purified by chromatography on silica gel (ethyl acetate) to give 40 mg of N-{4-[3-(4-Fluoro-phenyl)-6-methyl-1H-pyrrolo[3,2-b]pyridin-2-yl]-pyridin-2-yl}-malonamic acid methyl ester as white solid.

Workup

  1. customprepared
  2. customat room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentration the solid residue
  7. customis purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-ab6845a311914df4b65b481fae79bad1
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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