Acetic Acid → 2-Amino-4-(isopropylsulfonyl)-1-(N-2-pyrrolidine-1-ylethylamino)benzene

HRID 1817855Notes

Reaction equation

HRID 1817855 reaction equation
[CH:1]([S:4]([C:7]1[CH:20]=[CH:19][C:10]([NH:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:9]([N+:21]([O-])=O)[CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].C(O)(=O)C>C(OCC)(=O)C.[C].[Pd]>[NH2:21][C:9]1[CH:8]=[C:7]([S:4]([CH:1]([CH3:2])[CH3:3])(=[O:5])=[O:6])[CH:20]=[CH:19][C:10]=1[NH:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 68871059HCID 68871059, compound

Product 1

HCID 688708672-Amino-4-(isopropylsulfonyl)-1-(N-2-pyrrolidine-1-ylethylamino)benzeneYield 52%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of crude 4-(isopropylsulfonyl)-2-nitro-N-(2-pyrrolidin-1-ylethyl)aniline (Step A), 10% palladium carbon (20 mg) and acetic acid (0.2 mL) in ethyl acetate (5 mL) was stirred for 2 h at room temperature under H2 atmosphere then the reaction mixture was filtered. The filtrate was evaporated under reduced pressure. The residue was purified by amine coated silica gel column chromatography (hexane:ethyl acetate=1:2) to give the title compound as an orange solid (122.9 mg, 52%, 2 steps).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customThe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by amine coated silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-7314dcb10a3549fc8f417ed01b4827bc
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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