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

HRID 1052828Notes

Reaction equation

HRID 1052828 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][CH:19]=3)(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)=[C:6]([NH:26][C@H:27]([C:29]2[N:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:33](=[O:41])[C:32]3=[CH:42][CH:43]=[CH:44][N:31]3[N:30]=2)[CH3:28])[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:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)=[C:6]([NH:26][C@H:27]([C:29]2[N:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:33](=[O:41])[C:32]3=[CH:42][CH:43]=[CH:44][N:31]3[N:30]=2)[CH3:28])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118434036(S)-N-(3-(4-Amino-6-((1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)phenyl)-4-methoxybenzenesulfonamide

Product 1

HCID 90102013(S)-N-(3-(4-Amino-6-((1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)phenyl)-4-hydroxybenzenesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(3-(4-Amino-6-((1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)phenyl)-4-methoxybenzenesulfonamide (126 mg, 0.21 mmol) was treated with boron tribromide (1M in dichloromethane, 0.62 ml, 0.62 mmol) with dichloromethane (1.5 ml) as a solvent according to the method described in Example 23. The residue was purified by reverse phase chromatography using SP1® Purification System to give 47 mg (38% yield) as a solid. Purity 99%.

Workup

  1. customThe residue was purified by reverse phase chromatography
  2. customSP1® Purification System
  3. customto give 47 mg (38% yield) as a solid

Sources & evidence

ORD record
ord-f76549fa0fa54ef99a5ff530554a1a17
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…