1,1-Dimethylhydrazine → 4-chloro-N-[4-(N',N'-dimethyl-hydrazinocarbonyl)-2-fluoro-benzyl]-N-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-benzenesulfonamide

HRID 852006Notes

Reaction equation

HRID 852006 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][C:24]=2[F:32])[C@@H:12]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.CCN(C(C)C)C(C)C.[CH3:62][N:63]([CH3:65])[NH2:64]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([NH:64][N:63]([CH3:65])[CH3:62])=[O:29])=[CH:25][C:24]=2[F:32])[C@@H:12]2[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 59761,1-DimethylhydrazineHCID 81531DiisopropylethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 117127634-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid

Product 1

HCID 115554864-chloro-N-[4-(N',N'-dimethyl-hydrazinocarbonyl)-2-fluoro-benzyl]-N-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid (0.15 g, 0.30 mmol) was dissolved in DMF (20 ml) and treated with 2-(2-pyridon-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TPTU) (0.1 g, 0.33 mmol), Hünig's base (0.15 ml, 0.90 mmol) and N,N-dimethyl hydrazine (0.07 ml, 0.90 mmol). After 1 h the reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and washed with NaHCO3, KHSO4/K2SO4, brine, dried (Na2SO4) filtered anconcentrated under reduced pressure. Crystallisation from isopropyl acetate yielded 4-chloro-N-[4-(N′,N′-dimethyl-hydrazinocarbonyl)-2-fluoro-benzyl]-N-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-benzenesulfonamide as a crystalline solid: δ 0.12 g; MS: m/e=525.4 (MH+).

Workup

  1. concentrationAfter 1 h the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with NaHCO3, KHSO4/K2SO4, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customCrystallisation from isopropyl acetate

Sources & evidence

ORD record
ord-d0da1114dd324e5ca71bfbc190b399ac
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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