Tryptamine → HCID 86683893, compound

HRID 1620121Notes

Reaction equation

HRID 1620121 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1.N1(O[C:29]2[C:37]([F:38])=[CH:36][C:32]([C:33]([NH2:35])=[O:34])=[C:31]([NH:39][C:40]3[CH:45]=[C:44]([O:46][CH3:47])[CH:43]=[C:42]([O:48][CH3:49])[CH:41]=3)[N:30]=2)C2C=CC=CC=2N=N1.[Cl-].[Na+]>C(OCC)(=O)C.O.CN1CCCC1=O>[CH3:49][O:48][C:42]1[CH:41]=[C:40]([NH:39][C:31]2[N:30]=[C:29]([NH:7][CH2:8][CH2:9][C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[C:37]([F:38])=[CH:36][C:32]=2[C:33]([NH2:35])=[O:34])[CH:45]=[C:44]([O:46][CH3:47])[CH:43]=1

Participants

8

Reactant 4

HCID 1150Tryptamine2×HCID 5234Sodium ChlorideHCID 11430Potassium Carbonate2×HCID 86683891HCID 86683891, compound

Product 1

HCID 86683893HCID 86683893, compoundYield 43.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (27 mg) and tryptamine (32 mg) were added to an N-methylpyrrolidone (1 ml) solution containing 6-(1H-1,2,3-benzotriazol-1-yloxy)-2-(3,5-dimethoxyphenylamino)-5-fluoronicotinamide (41 mg), followed by stirring at 90° C. for 7 hours. The reaction mixture was cooled to room temperature, and potassium carbonate (14 mg) and tryptamine (16 mg) were added, followed by stirring at 90° C. for 7 hours. The reaction mixture was cooled to room temperature, and then water, sodium chloride, and ethyl acetate were added. The organic layer was collected and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (chloroform:methanol=10:0 to 20:1), diisopropylether was added, solid matter was collected by filtration, and a light brown solid of 2-(3,5-dimethoxyphenylamino)-5-fluoro-6-(2-(1H-indole-3-yl)ethylamino)nicotinamide (19 mg) was thus obtained.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring at 90° C. for 7 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography (chloroform:methanol=10:0 to 20:1), diisopropylether
  8. additionwas added
  9. filtrationsolid matter was collected by filtration

Sources & evidence

ORD record
ord-7c62d02fd4c446869a6a238f5955da25
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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