Boron tribromide → HCID 178513868, compound

HRID 869194Notes

Reaction equation

HRID 869194 reaction equation
[C:1]([CH:4]1[S:8][CH:7]([C:9]2[N:14]=[N:13][C:12]([N:15]([CH2:23][C:24]3([C:28]4[C:33]([F:34])=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:27][CH2:26][CH2:25]3)C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)[N:6]=[C:5]1[O:35]C)(=[O:3])[NH2:2].B(Br)(Br)Br>C(Cl)Cl.CO>[F:34][C:33]1[C:28]([C:24]2([CH2:23][NH:15][C:12]3[N:13]=[N:14][C:9]([CH:7]4[N:6]=[C:5]([OH:35])[CH:4]([C:1]([NH2:2])=[O:3])[S:8]4)=[CH:10][CH:11]=3)[CH2:25][CH2:26][CH2:27]2)=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 86686142HCID 86686142, compound

Product 1

HCID 178513868HCID 178513868, compoundYield 31,060.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring mixture of t-butyl 6-(5-carbamoyl-4-methoxy-2,5-dihydrothiazol-2-yl)pyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (60 mg, 0.12 μmol) in CH2Cl2 (2 mL) was added BBr3 (140 μL, 1.2 mmol). The reaction was stirred at rt for 2 h and then at 60° C. for 15 min. The reaction was cooled to rt and carefully diluted with methanol (2 mL). The reaction was concentrated, diluted with ethyl acetate (20 mL), and saturated sodium bicarbonate (10 mL) was added. The mixture was agitated and then filtered. The subsequent crude solid was then purified using reverse phase chromatography to give 15 mg of 2-(6-((1-(3-fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazin-3-yl)-4-hydroxy-2,5-dihydrothiazole-5-carboxamide as a yellow solid (M+H=401.3)

Workup

  1. waitat 60° C. for 15 min
  2. temperatureThe reaction was cooled to rt
  3. concentrationThe reaction was concentrated
  4. additiondiluted with ethyl acetate (20 mL), and saturated sodium bicarbonate (10 mL)
  5. additionwas added
  6. stirringThe mixture was agitated
  7. filtrationfiltered
  8. customThe subsequent crude solid was then purified

Sources & evidence

ORD record
ord-1293632d4f0240d59caad165084cc5aa
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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