Boron tribromide → HCID 178492874, compound

HRID 1052678Notes

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][CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]([O:14]C)=[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>>[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][CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]([OH:14])=[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

Reactant 2

HCID 25134Boron tribromide

HCID 118433881(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-methoxypyridin-3-yl)-4-methoxybenzenesulfonamide

Product 1

HCID 178492874HCID 178492874, compoundYield 46%

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-methoxypyridin-3-yl)-4-methoxybenzenesulfonamide (82 mg, 0.13 mmol) was treated with a solution of boron tribromide (1M in dichloromethane, 190 μl, 0.19 mmol) according to the method described in Example 23. The residue was purified using SP1® Purification System (0% to 100%, hexane-ethyl acetate) to give 37 mg (46% yield) of the title compound as a solid.

Workup

customThe residue was purified
customSP1® Purification System (0% to 100%, hexane-ethyl acetate)

Sources & evidence

ORD record: ord-d45ccce485074a38b566425a80ca6673
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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