p-Toluenesulfonic acid → 2-(4-((2-(2-Fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methylacetamide

HRID 1051010Notes

Reaction equation

HRID 1051010 reaction equation
C(OC(=O)[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[N:12]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH:32]3[CH2:37]CCCO3)=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:11]=1)[CH3:8])(C)(C)C.[F:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]1[N:50]([S:51]([C:54]2[CH:59]=[CH:58][C:57]([OH:60])=[CH:56][CH:55]=2)(=[O:53])=[O:52])[CH:49]=[C:48]([CH2:61][N:62]([CH3:70])[C:63](=[O:69])[O:64][C:65]([CH3:68])([CH3:67])[CH3:66])[CH:47]=1.C1(C)C=CC(S(O)(=O)=[O:78])=CC=1>CO>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]1[N:12]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:37]([NH:50][CH3:49])=[O:78])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:11]=[C:10]([CH2:9][NH:7][CH3:8])[CH:14]=1.[F:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]1[N:50]([S:51]([C:54]2[CH:55]=[CH:56][C:57]([OH:60])=[CH:58][CH:59]=2)(=[O:52])=[O:53])[CH:49]=[C:48]([CH2:61][N:62]([CH3:70])[C:63](=[O:69])[O:64][C:65]([CH3:66])([CH3:67])[CH3:68])[CH:47]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 131736094tert-Butyl ((5-(2-fluorophenyl)-1-((4-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate tert-Butyl ((5-(2-fluorophenyl)-1-((4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl) sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Product 2

HCID 747629982-(4-((2-(2-Fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methylacetamideHCID 90168684tert-butyl ((5-(2-fluorophenyl)-1-((4-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl ((5-(2-fluorophenyl)-1-((4-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate tert-Butyl ((5-(2-fluorophenyl)-1-((4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 4c (2.3 g, 4.28 mmol) was dissolved in 30 mL of methanol, followed by addition of p-toluenesulfonic acid (148 mg, 0.86 mmol), and then the reaction solution was stirred for 3 h. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with elution system B to obtain the title product tert-butyl ((5-(2-fluorophenyl)-1-((4-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 4d (2.0 g, a colorless oil) in 80% yield.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-c97d71aeaf6646e981c37e3cfe77ea21
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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