Water → (S)-N-(3-(2-(Dimethylamino)ethoxy)-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamide

HRID 1052753Notes

Reaction equation

HRID 1052753 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:5]=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[NH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].Cl[CH2:50][CH2:51][NH+:52]([CH3:54])[CH3:53].O>CN(C)C=O>[CH3:53][N:52]([CH3:54])[CH2:51][CH2:50][O:1][C:2]1[CH:3]=[C:4]([NH:37][S:38]([CH3:41])(=[O:39])=[O:40])[CH:5]=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[NH:10][CH:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 20717(2-Chloroethyl)dimethylamine, chlorideHCID 901023362,3-d]Pyrimidin-5-yl]-5-oxidanyl-phenyl]methanesulfonamide

Product 1

HCID 90102856(S)-N-(3-(2-(Dimethylamino)ethoxy)-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamideYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

(S)—N-(3-Hydroxy-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamide (6 mg, 0.01 mmol) was dissolved in 120 μl N,N-dimethylformamide. Sodium carbonate (8 mg, 0.07 mmol) and 2-chloro-N,N-dimethylethanaminium chloride (4 mg, 0.03 mmol) were added and the mixture was stirred at 50° C. overnight. The reaction was poured into water and extracted twice with ethyl acetate. The organics were combined and washed with brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System (0% to 100%, dichloromethane-dichloromethane/2-propanol 85:15) to give 4 mg (56% yield) of the title compound.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified
  7. customSP1® Purification System (0% to 100%, dichloromethane-dichloromethane/2-propanol 85:15)

Sources & evidence

ORD record
ord-3519fe54de6640d488dbb0549ce9a981
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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