Boron tribromide → (S)-N-(3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)phenyl)-2,4-dihydroxybenzenesulfonamide

HRID 1052846Notes

Reaction equation

HRID 1052846 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][C:19]=3[O:26]C)(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)=[C:6]([NH:28][C@H:29]([C:31]2[N:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:35](=[O:43])[C:34]3=[C:44]([CH3:47])[CH:45]=[CH:46][N:33]3[N:32]=2)[CH3:30])[N:5]=[CH:4][N:3]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:19]=3[OH:26])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)=[C:6]([NH:28][C@H:29]([C:31]2[N:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:35](=[O:43])[C:34]3=[C:44]([CH3:47])[CH:45]=[CH:46][N:33]3[N:32]=2)[CH3:30])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118433791(S)-N-(3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)phenyl)-2,4-dimethoxybenzenesulfonamide

Product 1

HCID 118433748(S)-N-(3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)phenyl)-2,4-dihydroxybenzenesulfonamideYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)phenyl)-2,4-dimethoxybenzenesulfonamide (108 mg, 0.17 mmol) was treated with boron tribromide (1M in dichloromethane, 0.90 ml, 0.9 mmol) with dichloromethane (20 ml) as a solvent at 100° C. for 2 h under microwave conditions. After evaporation of the solvent and usual workup with ethyl acetate and water, the residue was purified by reverse phase chromatography using SP1® Purification System to give 48 mg (55% yield) as a solid. Purity 99%.

Workup

  1. customAfter evaporation of the solvent and usual workup with ethyl acetate and water
  2. customthe residue was purified by reverse phase chromatography
  3. customSP1® Purification System
  4. customto give 48 mg (55% yield) as a solid

Sources & evidence

ORD record
ord-fc337281d04946a190664c5fcad0c626
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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