4-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-N-acetyl-benzenesulfonamide → 4-[(2-methylthio-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamide

HRID 1789661Notes

Reaction equation

HRID 1789661 reaction equation
B.C1COCC1.C1COCC1.[CH3:12][S:13][CH2:14][CH2:15][N:16]([C:30](=O)[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)[C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:26][C:27](=O)[CH3:28])(=[O:25])=[O:24])=[CH:19][CH:18]=1>C1COCC1>[CH3:12][S:13][CH2:14][CH2:15][N:16]([CH2:30][C:31]1[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=1)[C:17]1[CH:18]=[CH:19][C:20]([S:23]([NH:26][CH2:27][CH3:28])(=[O:24])=[O:25])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 220361694-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-N-acetyl-benzenesulfonamideHCID 178419153HCID 178419153, compound

Product 1

HCID 220362154-[(2-methylthio-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamideYield 60.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1 M BH3.THF/THF (7.0 mL, 7.0 mmol) was added to a stirring solution of 4-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-N-acetyl-benzenesulfonamide (0.29 g, 0.69 mmol) in THF (8 mL). After 18 h, the excess BH3 was quenched by addition of 0.1 M HCl; followed by partitioning the mixture between CH2Cl2 and NaHCO3. The organic layer was dried (Na2SO4), filtered, evaporated in vacuo, and the residue was purified by MPLC (CH2Cl2 to 90:10 CH2Cl2/EtOAc) to afford 0.16 g (59%) of 4-[(2-methylthio-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamide as a colorless glass; 1H NMR δ 1.09 (t, 3H, J=7.5), 2.16 (s, 3H), 2.74 (m, 2H), 2.96 (m, 2H), 3.67 (m, 2H), 4.37 (t, 1H, J=6.0), 4.62 (s, 2H), 6.69 (d, 2H, J=9.0), 7.04 (dd, 2H, J=4.5, 7.5), 7.15 (dd, 2H, J=6.0, 9.0), 7.66 (d, 2H, J=7.5).

Workup

  1. customthe excess BH3 was quenched by addition of 0.1 M HCl
  2. customby partitioning the mixture between CH2Cl2 and NaHCO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customthe residue was purified by MPLC (CH2Cl2 to 90:10 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-9ae83228f5ec4410b154a474b8f6e587
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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