Boron tribromide → HCID 178428097, compound

HRID 1052777Notes

Reaction equation

HRID 1052777 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:28]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[N:31]=[C:30]([O:38]C)[CH:29]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:28]1[CH:33]=[C:32]([C:34]([F:36])([F:37])[F:35])[N:31]=[C:30]([OH:38])[CH:29]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 90102241HCID 90102241, compound

Product 1

HCID 178428097HCID 178428097, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-2-(1-((6-Amino-5-(2-methoxy-6-(trifluoromethyl)pyridin-4-yl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (40 mg, 0.07 mmol) was dissolved in dichloromethane (1 ml). A solution of boron tribromide (1M in dichloromethane, 223 μl, 0.22 mmol) was added dropwise and the reaction mixture was stirred at room temperature overnight. Further boron tribromide (1M in dichloromethane, 223 μl, 0.22 mmol) was added and the reaction mixture stirred at room temperature an extra night. The reaction mixture was then 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 8 mg (20% yield) of the title compound as a white solid. Purity 99%.

Workup

  1. stirringthe reaction mixture stirred at room temperature an extra night
  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-0f89a63764fa4013b7ce7cc3caac2213
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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