Boron tribromide → HCID 90102388, compound

HRID 1052838Notes

Reaction equation

HRID 1052838 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:36]=[C:35]2[C:31]([CH:32]=[CH:33][N:34]2[S:37]([C:40]2[CH:45]=[CH:44][C:43]([O:46]C)=[CH:42][CH:41]=2)(=[O:39])=[O:38])=[CH:30][CH:29]=1.B(Br)(Br)Br>ClCCl.C(OCC)(=O)C>[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:36]=[C:35]2[C:31]([CH:32]=[CH:33][N:34]2[S:37]([C:40]2[CH:41]=[CH:42][C:43]([OH:46])=[CH:44][CH:45]=2)(=[O:38])=[O:39])=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 25134Boron tribromide2×HCID 90102565HCID 90102565, compound

Product 1

HCID 90102388HCID 90102388, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-(1-((6-Amino-5-(1-((4-methoxyphenyl)sulfonyl)-1H-indol-6-yl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (100 mg, 0.14 mmol) was dissolved in dichloromethane (1 ml). A solution of boron tribromide (1M in dichloromethane, 952 μL, 0.95 mmol) was added dropwise and the reaction was stirred at room temperature overnight. A solution of boron tribromide (1M in dichloromethane, 1.4 ml, 1.4 mmol) was added dropwise and the reaction was heated at 60° C. overnight. The mixture was diluted with ethyl acetate and washed with a 4% solution of sodium bicarbonate, water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure. The product was purified by reverse phase chromatography using SP1® Purification System to give 53 mg (61% yield) of the title compound. Purity 99%. LRMS (m/z): 633 (M+1)+.

Workup

  1. temperaturethe reaction was heated at 60° C. overnight
  2. washwashed with a 4% solution of 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 chromatography
  7. customSP1® Purification System

Sources & evidence

ORD record
ord-0e29b9f4f95b4f31b6595e6ad47755e2
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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