Boron tribromide → HCID 90102538, compound

HRID 1052740Notes

Reaction equation

HRID 1052740 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:13]([NH:18][C@H:19]([C:21]3[N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25](=[O:33])[C:24]4=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]4[N:22]=3)[CH3:20])=[N:14][CH:15]=[N:16][CH:17]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:13]([NH:18][C@H:19]([C:21]3[N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25](=[O:33])[C:24]4=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]4[N:22]=3)[CH3:20])=[N:14][CH:15]=[N:16][CH:17]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118433895HCID 118433895, compound

Product 1

HCID 90102538HCID 90102538, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(3-Methoxyphenyl)-4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamide (80 mg, 72% purity, 0.12 mmol) was treated with boron tribromide (1M in dichloromethane, 0.6 ml, 0.6 mmol) in dichloromethane (2 ml) according to the method described in Example 23. The residue was purified using SP1® Purification System (0% to 10%, DCM-MeOH) to give 8 mg (14% yield) as a solid. Purity 95%.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 10%, DCM-MeOH)
  3. customto give 8 mg (14% yield) as a solid

Sources & evidence

ORD record
ord-291ac30b948e4938a30aa5cd5a50c73a
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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