Hydrochloric Acid → (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

HRID 1052389Notes

Reaction equation

HRID 1052389 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[CH:40][C:6]([CH2:7][NH:8][C:9]2[C:14]([C:15]([O:17]CC)=[O:16])=[C:13]([NH:20][C@H:21]([C:23]3[N:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:27](=[O:35])[C:26]4=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]4[N:24]=3)[CH3:22])[N:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[Li+].Cl>C(O)C.O1CCCC1.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]([OH:17])=[O:16])=[C:13]([NH:20][C@H:21]([C:23]3[N:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:27](=[O:35])[C:26]4=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]4[N:24]=3)[CH3:22])[N:12]=[CH:11][N:10]=2)=[CH:40][CH:41]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 131736128(S)-Ethyl 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-carboxylate

Product 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 acidYield 111.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(S)-Ethyl 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-carboxylate (281 mg, 0.51 mmol) was dissolved in 2 mL ethanol and 3 mL tetrahydrofuran. Lithium hydroxide (213 mg, 50.8 mmol) in 3 mL water was added and the mixture was heated at 50° C. overnight. Further lithium hydroxide (213 mg, 50.8 mmol) in 3 mL water was added and the reaction mixture heated at 50° C. for 4 h more. The reaction mixture was diluted with water and acidified to pH 5 with hydrochloric acid 5N. The aqueous phase was extracted with ethyl acetate and the organics were washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure to give 300 mg (99% yield) of the title compound as a white solid. Purity 90%.

Workup

  1. temperaturethe reaction mixture heated at 50° C. for 4 h more
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe organics were washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1205d360b445424f949d235430b9bc51
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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