Hydrochloric Acid → HCID 90168588, compound

HRID 1051031Notes

Reaction equation

HRID 1051031 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([NH:26][CH2:27][CH2:28][OH:29])=[O:25])[CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:30][N:31](C)[C:32](=O)OC(C)(C)C)[CH:9]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=2)[O:22][CH2:23][C:24]([NH:26][CH2:27][CH2:28][OH:29])=[O:25])(=[O:14])=[O:15])[CH:11]=[C:10]([CH2:30][NH:31][CH3:32])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90168787HCID 90168787, compound

Product 1

HCID 90168588HCID 90168588, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl ((5-(2-fluorophenyl)-1-((3-(2-((2-hydroxyethyl)amino)-2-oxoethoxy) phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 10a (83 mg, 0.15 mmol) was added to a solution of hydrogen chloride in 1,4-dioxane (4 N, 20 mL), and then the reaction solution was stirred for 2 h. The pH of the reaction solution was adjusted to 7 to 8 with a saturated sodium bicarbonate solution, and it was extracted with dichloromethane (50 mL×2). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by thin layer chromatography with elution system A to obtain the title product 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-(2-hydroxyethyl)acetamide 10 (34 mg, a yellow oil) in 50% yield.

Workup

  1. extractionwas extracted with dichloromethane (50 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by thin layer chromatography with elution system

Sources & evidence

ORD record
ord-79a4129ae5c54ae98ef7d7fa02fe7192
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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