Boron tribromide → (S)-N-(5-(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)-2-ethylpyridin-3-yl)-4-hydroxybenzenesulfonamide

HRID 1052824Notes

Reaction equation

HRID 1052824 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]([CH2:14][CH3:15])=[N: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:16][S:17]([C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)(=[O:19])=[O:18])[C:11]([CH2:14][CH3:15])=[N: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 118433860(S)-N-(5-(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)-2-ethylpyridin-3-yl)-4-methoxybenzenesulfonamide

Product 1

HCID 118433940(S)-N-(5-(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)-2-ethylpyridin-3-yl)-4-hydroxybenzenesulfonamideYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(5-(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)-2-ethylpyridin-3-yl)-4-methoxybenzenesulfonamide (146 mg, 0.22 mmol) was treated with boron tribromide (1M in dichloromethane, 700 μl, 0.70 mmol) in dichloromethane (1 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 31 mg (22% yield) as a solid. Purity 100%.

Workup

  1. customThe residue was purified by reverse phase chromatography
  2. customSP1® Purification System
  3. customto give 31 mg (22% yield) as a solid

Sources & evidence

ORD record
ord-659979768cd045e191697b69a1badb91
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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