Diisopropylamine → 4-(1-(2,2-Difluoroethyl)piperidin-4-ylamino)-3-nitrobenzenesulfonamide

HRID 706894Notes

Reaction equation

HRID 706894 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([S:18]([NH2:21])(=[O:20])=[O:19])[CH:8]=[CH:9][C:10]=1[NH:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([O-:4])=[O:3].[F:22][CH:23]([F:26])[CH2:24]I.C(NC(C)C)(C)C>CN(C)C=O.ClCCl>[F:22][CH:23]([F:26])[CH2:24][N:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:10]2[CH:9]=[CH:8][C:7]([S:18]([NH2:21])(=[O:19])=[O:20])=[CH:6][C:5]=2[N+:2]([O-:4])=[O:3])[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 38335651,1-Difluoro-2-iodoethaneHCID 67170227HCID 67170227, compound

Product 1

HCID 489340074-(1-(2,2-Difluoroethyl)piperidin-4-ylamino)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

3-nitro-4-(piperidin-4-ylamino)benzenesulfonamide hydrochloride (0.100 g), 1,1-difluoro-2-iodoethane (0.063 mL) and diisopropylamine (0.156 mL) were stirred together in N,N-dimethylformamide (3 ml) and heated to 85° C. The reaction was diluted with dichloromethane (50 mL) and washed with water (50 mL), brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. The residue was loaded onto silica gel (GraceResolve 12 g) and eluted using a gradient of 0.5% methanol/dichloromethane to 3% methanol/dichloromethane over 30 minutes to give the title compound.

Workup

  1. washwashed with water (50 mL), brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluted
  6. customover 30 minutes

Sources & evidence

ORD record
ord-cdcfda44ec854b19874c028fd1075c00
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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