(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 → (S)-4-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 1052391Notes

Reaction equation

HRID 1052391 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)=[O:16])=[C:13]([NH:26][C@H:27]([C:29]3[N:34]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:33](=[O:41])[C:32]4=[C:42]([CH3:45])[CH:43]=[CH:44][N:31]4[N:30]=3)[CH3:28])[N:12]=[CH:11][N:10]=2)=CC=1>FC(F)(F)C(O)=O>[NH2:8][C:9]1[C:14]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)=[O:16])=[C:13]([NH:26][C@H:27]([C:29]2[N:34]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:33](=[O:41])[C:32]3=[C:42]([CH3:45])[CH:43]=[CH:44][N:31]3[N:30]=2)[CH3:28])[N:12]=[CH:11][N:10]=1

Participants

3

Reactant 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-carboxamide

Product 1

HCID 118433742(S)-4-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 28%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(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 (120 mg, 0.19 mmol) was dissolved in 5 mL trifluoroacetic acid. The reaction mixture was stirred at room temperature overnight. The trifluoroacetic acid was evaporated and the crude was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulphate, filtered and concentrated. The residue was purified by reverse phase using SP1® Purification System to obtain 27 mg (28% yield) of the title compound.

Workup

  1. customThe trifluoroacetic acid was evaporated
  2. customthe crude was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase
  8. custom® Purification System

Sources & evidence

ORD record
ord-1e608b8d4f8245e6b857ac7ada44f532
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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