Ammonia → 5-(3,5-Di-tert-butylphenyl)-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-sulfonamide

HRID 1844717Notes

Reaction equation

HRID 1844717 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15]2[N:16]([S:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)(=[O:23])=[O:22])[C:17]([CH3:20])=[CH:18][CH:19]=2)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl[S:31]([OH:34])(=O)=[O:32].[NH3:35]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([C:15]2[N:16]([S:21]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)(=[O:22])=[O:23])[C:17]([CH3:20])=[C:18]([S:31]([NH2:35])(=[O:34])=[O:32])[CH:19]=2)[CH:8]=[C:9]([C:11]([CH3:13])([CH3:14])[CH3:12])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24638Chlorosulfonic acidHCID 867191321-((2-(3,5-Di-tert-butylphenyl)-5-methyl-1H-pyrrol-1-yl)sulfonyl)piperidine

Product 1

HCID 709134055-(3,5-Di-tert-butylphenyl)-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-sulfonamideYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 4e (195 mg, 0.46 mmol) in DCM (0.9 mL) was added ClSO3H (0.45 mL, 7.02 mmol) at −40° C. under Ar. The mixture was slowly warmed to rt and stirred for 48 h. To the mixture was added dropwise to NH3 (3N in THF, 20 mL) at −20° C. and the mixture was stirred for 2 h, evaporated, redissolved in water, extracted with EA, washed with brine, dried with Na2SO4, concentrated and purified by prep-HPLC to afford compound 4 (16 mg, 8%) as light yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 8.28 (s, 1H), 7.49 (t, J=1.8 Hz, 1H), 7.33 (d, J=1.6 Hz, 2H), 5.71 (s, 2H), 2.88 (m, 4H), 2.57 (s, 3H), 1.35-1.27 (m, 24H). LC-MS (ESI+) m/z: 496.6 [M+1]+.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. customevaporated
  3. dissolutionredissolved in water
  4. extractionextracted with EA
  5. washwashed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-abe2d18ccae6415da77a2e0fe28c5bb1
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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