Cesium fluoride → (S)-2-(1-((5-((4-Aminophenyl)thio)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052597Notes

Reaction equation

HRID 1052597 reaction equation
Cl[C:2]1[C:3]2[C:10]([S:11][C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=3)=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:4]=2[N:5]=[CH:6][N:7]=1.[Cl-].[CH3:28][C:29]1[CH:30]=[CH:31][N:32]2[C:37]=1[C:36](=[O:38])[N:35]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:34]([C@@H:45]([NH3+:47])[CH3:46])=[N:33]2.[F-].[Cs+].C(N(CC)C(C)C)(C)C>C(O)(C)(C)C>[NH2:16][C:15]1[CH:17]=[CH:18][C:12]([S:11][C:10]2[C:3]3[C:2]([NH:47][C@H:45]([C:34]4[N:35]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[C:36](=[O:38])[C:37]5=[C:29]([CH3:28])[CH:30]=[CH:31][N:32]5[N:33]=4)[CH3:46])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:9]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 90102579(S)-1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethanaminium chlorideHCID 1317362204-((4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)thio)aniline

Product 1

HCID 131736221(S)-2-(1-((5-((4-Aminophenyl)thio)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 42.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

4-((4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)thio)aniline (350 mg, 0.73 mmol) was treated with (S)-1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethanaminium chloride (215 mg, 0.80 mmol), cesium fluoride (11 mg, 0.07 mmol), N,N-diisopropylethylamine (318 μl, 1.83 mmol) and tert-butanol (4 ml) as a solvent according to Preparation 163. The residue was purified by reverse phase using SP1® Purification System to obtain 200 mg (40% yield) of the title compound. Yield 98%.

Workup

  1. customaccording to Preparation 163
  2. customThe residue was purified by reverse phase
  3. custom® Purification System

Sources & evidence

ORD record
ord-5cd6634b481f4092a39fe85c95659f2f
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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