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-(ethylamino)pyridin-3-yl)-4-hydroxybenzenesulfonamide

HRID 1052848Notes

Reaction equation

HRID 1052848 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:11]([NH:14][CH2:15][CH3:16])=[N:12][CH:13]=2)=[C:6]([NH:29][C@H:30]([C:32]2[N:37]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:36](=[O:44])[C:35]3=[C:45]([CH3:48])[CH:46]=[CH:47][N:34]3[N:33]=2)[CH3:31])[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:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:11]([NH:14][CH2:15][CH3:16])=[N:12][CH:13]=2)=[C:6]([NH:29][C@H:30]([C:32]2[N:37]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:36](=[O:44])[C:35]3=[C:45]([CH3:48])[CH:46]=[CH:47][N:34]3[N:33]=2)[CH3:31])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118433803HCID 118433803, compound

Product 1

HCID 118433804(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-(ethylamino)pyridin-3-yl)-4-hydroxybenzenesulfonamideYield 32%

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-(ethylamino)pyridin-3-yl)-4-methoxybenzenesulfonamide (18 mg, 0.03 mmol) was treated with boron tribromide (1M in dichloromethane, 0.1 ml, 0.10 mmol) with dichloromethane (1 ml) as a solvent according to the method described in Example 23. The residue was purified by reverse phase using SP1® Purification System to give 6 mg (32% yield) as a solid. Purity 93%.

Workup

  1. customThe residue was purified by reverse phase
  2. custom® Purification System
  3. customto give 6 mg (32% yield) as a solid

Sources & evidence

ORD record
ord-de79a964380344108d1478e13d045e6e
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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