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)pyridin-3-yl)-4-hydroxybenzenesulfonamide

HRID 1052762Notes

Reaction equation

HRID 1052762 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]=[N: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=[C:42]([CH3:45])[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:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:11]=[N: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=[C:42]([CH3:45])[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 118433907(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)pyridin-3-yl)-4-methoxybenzenesulfonamide

Product 1

HCID 90103096(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)pyridin-3-yl)-4-hydroxybenzenesulfonamideYield 15%

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)pyridin-3-yl)-4-methoxybenzenesulfonamide (132 mg, 0.11 mmol) was treated with boron tribromide (1M in dichloromethane, 337 μl, 0.34 mmol) in dichloromethane (10 ml) according to the method described in Example 23. The residue was purified by reverse phase using SP1® Purification System to give 10 mg (15% yield) as a solid. Purity 99%.

Workup

  1. customThe residue was purified by reverse phase
  2. custom® Purification System
  3. customto give 10 mg (15% yield) as a solid

Sources & evidence

ORD record
ord-15730730733048328611046dd5e237e6
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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