Pyridine → N-(3-(6-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-3-yl)phenyl)acetamide

HRID 2192268Notes

Reaction equation

HRID 2192268 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:18](=[CH:19][C:20]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[CH:21][CH:22]=3)[N:17]([C:32]3[N:37]=[CH:36][N:35]=[C:34]([NH:38][CH3:39])[CH:33]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([C:20]2[CH:19]=[C:18]3[C:23]([C:15]([C:11]4[CH:10]=[C:9]([NH:8][C:1](=[O:3])[CH3:2])[CH:14]=[CH:13][CH:12]=4)=[CH:16][N:17]3[C:32]3[CH:33]=[C:34]([NH:38][CH3:39])[N:35]=[CH:36][N:37]=3)=[CH:22][CH:21]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 509918426-(3-(3-aminophenyl)-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Product 1

HCID 50991843N-(3-(6-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-3-yl)phenyl)acetamideYield 45.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (20.3 μL, 0.214 mmol) was added to a mixture solution of 6-(3-(3-aminophenyl)-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (30 mg, 0.071 mmol) and pyridine (28.7 μL, 0.355 mmol) in methylene chloride (2 mL) at room temperature. After stirring for 1 hour at room temperature, the reaction solution was added to saturated sodium bicarbonate aqueous solution and then extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (preparative HPLC). The target compound (15 mg) was obtained as white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe collected organic layer was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. dry with materialby drying with anhydrous magnesium sulfate
  5. customThe residue was purified by chromatography (preparative HPLC)

Sources & evidence

ORD record
ord-f79b1921b01f41bbb7018b3780b638b3
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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