Hydrochloric Acid → HCID 90168592, compound

HRID 1051032Notes

Reaction equation

HRID 1051032 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][CH2:29][OH:30])=[O:25])[CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:31][N:32](C)[C:33](=O)OC(C)(C)C)[CH:9]=1.Cl.[C:42](=O)(O)[O-].[Na+].[O:47]1[CH2:52][CH2:51]OCC1>ClCCl>[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][C:27]2[CH:28]=[CH:29][CH:42]=[C:52]([OH:47])[CH:51]=2)=[O:25])(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:31][NH:32][CH3:33])[CH:9]=1.[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][CH2:29][OH:30])=[O:25])(=[O:14])=[O:15])[CH:11]=[C:10]([CH2:31][NH:32][CH3:33])[CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 90168926HCID 90168926, compound

Product 2

HCID 90168592HCID 90168592, compoundHCID 118377313HCID 118377313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl ((5-(2-fluorophenyl)-1-((3-(2-((3-hydroxypropyl)amino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 11a (99 mg, 0.17 mmol) was dissolved in 5 mL of dichloromethane, and the reaction solution was cooled in an ice bath, followed by dropwise addition of a solution of hydrogen chloride in 1,4-dioxane (4 N, 2 mL), and then the reaction solution was stirred for 3 h. The pH of the reaction solution was adjusted to 7 to 8 with the 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-(3-hydroxypropyl)acetamide 11 (80 mg, a light yellow oil) in 97% yield.

Workup

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

Sources & evidence

ORD record
ord-0d994a0ca67e4231848c7fea3bd80ad6
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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