4-Fluoro-3-nitrobenzenesulfonamide → 4-[[(3R)-1-(2,2-Difluoroethyl)-3-pyrrolidinyl]amino]-3-nitrobenzenesulfonamide

HRID 1520657Notes

Reaction equation

HRID 1520657 reaction equation
[F:1][CH:2]([F:10])[CH2:3][N:4]1[CH2:8][CH2:7][C@@H:6]([NH2:9])[CH2:5]1.F[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23]>O1CCCC1.C(N(C(C)C)C(C)C)C.CN(C)C=O>[F:1][CH:2]([F:10])[CH2:3][N:4]1[CH2:8][CH2:7][C@@H:6]([NH:9][C:12]2[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][C:13]=2[N+:22]([O-:24])=[O:23])[CH2:5]1

Participants

6

Reactant 2

HCID 167824874-Fluoro-3-nitrobenzenesulfonamideHCID 79005005HCID 79005005, compound

Product 1

HCID 872946774-[[(3R)-1-(2,2-Difluoroethyl)-3-pyrrolidinyl]amino]-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of EXAMPLE 407B (468 mg) in tetrahydrofuran (20 mL), N-ethyl-N-isopropylpropan-2-amine (2.193 mL) and N,N-dimethylformamide (2 mL) was added 4-fluoro-3-nitrobenzenesulfonamide (473 mg) and the reaction mixture was stirred 72 hours. The crude product was isolated by concentration and was purified on silica gel, and was eluted with a 0.5, 2.5, and 5% methanol in methylene chloride step gradient to obtain the title compound.

Workup

  1. customThe crude product was isolated by concentration
  2. customwas purified on silica gel
  3. washwas eluted with a 0.5, 2.5, and 5% methanol in methylene chloride step gradient

Sources & evidence

ORD record
ord-0029bcf1440e45529fd1cd8de7be09b1
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

Loading…