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

HRID 1052595Notes

Reaction equation

HRID 1052595 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[C:17]3[C:16]([NH:18][C@H:19]([C:21]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:25](=[O:33])[C:24]5=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]5[N:22]=4)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[N:11]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>>[CH3:37][C:34]1[CH:35]=[CH:36][N:23]2[C:24]=1[C:25](=[O:33])[N:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]([C@@H:19]([NH:18][C:16]1[C:17]3[C:9]([S:8][C:4]4[CH:3]=[C:2]([NH:1][S:47]([CH3:46])(=[O:49])=[O:48])[CH:7]=[CH:6][CH:5]=4)=[CH:10][N:11]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:45])[CH3:44])[C:12]=3[N:13]=[CH:14][N:15]=1)[CH3:20])=[N:22]2

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 131736218(S)-2-(1-((5-((3-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

Product 1

HCID 131736219(S)-N-(3-((4-((1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)thio)phenyl)methanesulfonamideYield 23%

Procedure

(S)-2-(1-((5-((3-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 (100 mg, 0.13 mmol) was treated with methanesulfonyl chloride (10 μl, 0.14 mmol) according to the method described in Preparation 15b. The residue was purified by reverse phase using SP1® Purification System to give 20 mg (23% yield) of the title compound. Purity 98%.

Workup

  1. customThe residue was purified by reverse phase
  2. custom® Purification System

Sources & evidence

ORD record
ord-65394a9452474d3ab5ce60fea9fd8fad
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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