Diisopropylethylamine → (R)-4-(1-(1,3-difluoropropan-2-yl)pyrrolidin-3-ylamino)-3-nitrobenzenesulfonamide

HRID 573157Notes

Reaction equation

HRID 573157 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[F:15][CH2:16][CH:17]([N:20]1[CH2:24][CH2:23][C@@H:22]([NH2:25])[CH2:21]1)[CH2:18][F:19].C(N(C(C)C)C(C)C)C>O1CCCC1>[F:19][CH2:18][CH:17]([N:20]1[CH2:24][CH2:23][C@@H:22]([NH:25][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:21]1)[CH2:16][F:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 167824874-Fluoro-3-nitrobenzenesulfonamideHCID 67126443(R)-1-(1,3-difluoropropan-2-yl)pyrrolidin-3-amine

Product 1

HCID 67126648(R)-4-(1-(1,3-difluoropropan-2-yl)pyrrolidin-3-ylamino)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-fluoro-3-nitrobenzenesulfonamide (0.272 g) and (R)-1-(1,3-difluoropropan-2-yl)pyrrolidin-3-amine (0.195 g) in tetrahydrofuran (3.0 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.512 mL) and the reaction was stirred at room temperature. After stirring for 6 hours, the reaction was concentrated, loaded onto silica gel (Reveleris 40 g) and the product was purified by flash chromatography using a gradient of 25% to 100% ethyl acetate/hexanes over 30 minutes to provide the title compound.

Workup

  1. stirringAfter stirring for 6 hours
  2. concentrationthe reaction was concentrated
  3. customthe product was purified by flash chromatography
  4. customover 30 minutes

Sources & evidence

ORD record
ord-96288efd1ec746dbbebccc3776f58424
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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