3-Methoxyaniline → (S)-4-((4-Methoxybenzyl)amino)-N-(3-methoxyphenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamide

HRID 1052390Notes

Reaction equation

HRID 1052390 reaction equation
[CH3:1][O:2][C:3]1[CH:39]=[CH:38][C:6]([CH2:7][NH:8][C:9]2[C:14]([C:15]([OH:17])=O)=[C:13]([NH:18][C@H:19]([C:21]3[N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25](=[O:33])[C:24]4=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]4[N:22]=3)[CH3:20])[N:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:73][O:74][C:75]1[CH:76]=[C:77]([CH:79]=[CH:80][CH:81]=1)[NH2:78]>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[C:14]([C:15]([NH:78][C:77]3[CH:79]=[CH:80][CH:81]=[C:75]([O:74][CH3:73])[CH:76]=3)=[O:17])=[C:13]([NH:18][C@H:19]([C:21]3[N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25](=[O:33])[C:24]4=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]4[N:22]=3)[CH3:20])[N:12]=[CH:11][N:10]=2)=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 108243-MethoxyanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118434092(S)-4-((4-Methoxybenzyl)amino)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxylic acid

Product 1

HCID 118433963(S)-4-((4-Methoxybenzyl)amino)-N-(3-methoxyphenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamideYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-4-((4-Methoxybenzyl)amino)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxylic acid (300 mg, 0.51 mmol) was dissolved in 7 mL dimethylformamide. N,N-Diisopropylethylamine (150 μl, 1.10 mmol) and HATU (400 mg, 1.05 mmol) were added and the reaction mixture was stirred at room temperature for 30 min. Then, 3-methoxyaniline (95 μl, 0.85 mmol) was added and the reaction mixture stirred at room temperature overnight. The crude was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulphate and concentrated under reduced pressure. A semi-solid was obtained and purified using SP1® Purification System (0% to 50%, hexane-ethyl acetate) to obtain 265 mg (82% yield) of the title compound. Purity 100%.

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customA semi-solid was obtained
  7. custompurified
  8. customSP1® Purification System (0% to 50%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f6877a5ea2d7473cb0506360c25cbfdb
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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