Triethylamine → HCID 68291868, compound

HRID 877800Notes

Reaction equation

HRID 877800 reaction equation
I.[Br:2][C:3]1[CH:4]=[C:5]2[C:10]([NH:11][C@H:12]3[C@@H:16]([CH2:17][F:18])[CH2:15][NH:14][CH2:13]3)=[C:9]([C:19]([NH2:21])=[O:20])[CH:8]=[N:7][N:6]2[CH:22]=1.CCN(CC)CC.[CH3:30][S:31](Cl)(=[O:33])=[O:32].CCOC(C)=O>CN(C=O)C>[Br:2][C:3]1[CH:4]=[C:5]2[C:10]([NH:11][C@H:12]3[C@@H:16]([CH2:17][F:18])[CH2:15][N:14]([S:31]([CH3:30])(=[O:33])=[O:32])[CH2:13]3)=[C:9]([C:19]([NH2:21])=[O:20])[CH:8]=[N:7][N:6]2[CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 86707903HCID 86707903, compound

Product 1

HCID 68291868HCID 68291868, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-4-(((3S,4S)-4-(fluoromethyl)pyrrolidin-3-yl)amino) pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide salt (894 mg, 2.846 mmol) and Et3N (1.399 mL, 10.04 mmol) in DMF (10 mL) was added METHANESULFONYL CHLORIDE (0.293 mL, 3.76 mmol) and the resulting mixture was stirred at RT for 30 minutes. To the reaction mixture was then added 150 mL of EtOAc and the mixture was washed with 50 mL×2 of 10% LiCl solution, 50 mL of brine and then dried over Na2SO4. Filtration and concentration afforded a crude product which was triturated with MeOH and the resulting solid collected and dried under vacuum to afford the title compound (0.719 g, 90% yield). MS (ES+) m/z: 434.1, 436.1 (M+H); HPLC: 89.6%, retention time: 2.348 min (analytical HPLC Method H).

Workup

  1. washthe mixture was washed with 50 mL×2 of 10% LiCl solution, 50 mL of brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and concentration
  4. customafforded a crude product which
  5. customwas triturated with MeOH
  6. customthe resulting solid collected
  7. customdried under vacuum

Sources & evidence

ORD record
ord-bfcc272254ba49dfa5cd4e052a504fb2
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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