Boron tribromide → HCID 118433813, compound

HRID 1052863Notes

Reaction equation

HRID 1052863 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[CH:17]=3)[CH:11]=[N:12][CH:13]=2)=[C:6]([NH:25][C@H:26]([C:28]2[N:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:32](=[O:40])[C:31]3=[C:41]([CH3:44])[CH:42]=[CH:43][N:30]3[N:29]=2)[CH3:27])[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:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[CH:11]=[N:12][CH:13]=2)=[C:6]([NH:25][C@H:26]([C:28]2[N:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:32](=[O:40])[C:31]3=[C:41]([CH3:44])[CH:42]=[CH:43][N:30]3[N:29]=2)[CH3:27])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 118433785HCID 118433785, compound

Product 1

HCID 118433813HCID 118433813, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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)pyridin-3-yl)-3-methoxybenzamide (95 mg, 0.16 mmol) was dissolved in dichloromethane (3 ml). A solution of boron tribromide (1M in dichloromethane, 480 μl, 0.48 mmol) was added dropwise and the reaction was stirred at room temperature overnight. More solution of boron tribromide (1M in dichloromethane, 240 μL, 0.24 mmol) was added and the reaction was stirred at room temperature for 4 h. The mixture was diluted with dichloromethane and washed with a solution of 4% sodium bicarbonate, water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure. The product was purified by reverse phase using SP1® Purification System to give 45 mg (49% yield) of the title compound as a white solid. Purity 100%.

Workup

  1. stirringthe reaction was stirred at room temperature for 4 h
  2. washwashed with a solution of 4% sodium bicarbonate, water, brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe product was purified by reverse phase
  7. custom® Purification System

Sources & evidence

ORD record
ord-1d63c6d820da48209e023704d54d7d61
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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