Boron tribromide → (S)-N-(3-(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)-5-hydroxyphenyl)-4-hydroxybenzenesulfonamide

HRID 1052759Notes

Reaction equation

HRID 1052759 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:11]=[C:12]([OH:14])[CH:13]=2)=[C:6]([NH:27][C@H:28]([C:30]2[N:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:34](=[O:42])[C:33]3=[C:43]([CH3:46])[CH:44]=[CH:45][N:32]3[N:31]=2)[CH3:29])[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:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:11]=[C:12]([OH:14])[CH:13]=2)=[C:6]([NH:27][C@H:28]([C:30]2[N:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:34](=[O:42])[C:33]3=[C:43]([CH3:46])[CH:44]=[CH:45][N:32]3[N:31]=2)[CH3:29])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118433888(S)-N-(3-(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)-5-hydroxyphenyl)-4-methoxybenzenesulfonamide

Product 1

HCID 73776216(S)-N-(3-(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)-5-hydroxyphenyl)-4-hydroxybenzenesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(3-(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)-5-hydroxyphenyl)-4-methoxybenzenesulfonamide (25 mg, 0.04 mmol) was treated with boron tribromide (1M in dichloromethane, 118 μl, 0.12 mmol) in dichloromethane (3 ml) according to the method described in Example 23. The residue was purified by reverse phase using SP1® Purification System to give 10 mg (38% yield) as a solid. Purity 93%.

Workup

  1. customThe residue was purified by reverse phase
  2. custom® Purification System
  3. customto give 10 mg (38% yield) as a solid

Sources & evidence

ORD record
ord-9b5684e4d4b64e309ddc3f33f75ba163
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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