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

HRID 1052737Notes

Reaction equation

HRID 1052737 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([C:17](=[O:19])[NH2:18])[CH:14]=[CH:13][C:12]=2[O:20]C)=[O:9])=[C:6]([NH:22][C@H:23]([C:25]2[N:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:29](=[O:37])[C:28]3=[C:38]([CH3:41])[CH:39]=[CH:40][N:27]3[N:26]=2)[CH3:24])[N:5]=[CH:4][N:3]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([C:17](=[O:19])[NH2:18])[CH:14]=[CH:13][C:12]=2[OH:20])=[O:9])=[C:6]([NH:22][C@H:23]([C:25]2[N:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:29](=[O:37])[C:28]3=[C:38]([CH3:41])[CH:39]=[CH:40][N:27]3[N:26]=2)[CH3:24])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118433811(S)-4-Amino-N-(5-carbamoyl-2-methoxyphenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamide

Product 1

HCID 73776214(S)-4-Amino-N-(5-carbamoyl-2-hydroxyphenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamideYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4-Amino-N-(5-carbamoyl-2-methoxyphenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamide (400 mg, 49% purity, 0.35 mmol) was treated with boron tribromide (1M in dichloromethane, 1.1 ml, 1 mmol) in dichloromethane (8 ml) according to the method described in Example 23. The residue was purified by reverse phase using SP1® Purification System to give 10 mg (5% yield) as a solid. Purity 90%.

Workup

  1. customThe residue was purified by reverse phase
  2. custom® Purification System
  3. customto give 10 mg (5% yield) as a solid

Sources & evidence

ORD record
ord-a758cd6eb45846d78b50382ecb4e6bb0
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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