Triethylamine → HCID 9830595, compound

HRID 618381Notes

Reaction equation

HRID 618381 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:7](=[O:14])[N:8]([CH2:9][C:10]([F:13])([F:12])[F:11])[C:4]=2[CH:3]=1.[O:23]=[S:24]1(=[O:40])[C:28]2[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:27]=2[C:26](=[O:34])[N:25]1[CH2:35][CH2:36][CH2:37][CH2:38]Br.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[O:40]=[S:24]1(=[O:23])[C:28]2[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:27]=2[C:26](=[O:34])[N:25]1[CH2:35][CH2:36][CH2:37][CH2:38][N:18]1[CH2:19][CH2:20][CH:15]([N:6]2[C:5]3[CH:21]=[CH:22][C:2]([F:1])=[CH:3][C:4]=3[N:8]([CH2:9][C:10]([F:12])([F:13])[F:11])[C:7]2=[O:14])[CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 133659801,2-Benzisothiazol-3(2H)-one, 2-(4-bromobutyl)-5-chloro-, 1,1-dioxideHCID 18695982HCID 18695982, compound

Product 1

HCID 9830595HCID 9830595, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

The 4-(5-fluoro-3-(2,2,2-trifluoroethyl)-2-oxo-1-benzimidazolinyl)piperidine (~10 mmol.) above was dissolved in anhydrous DMF (25 mL) followed by the addition of 1,1 -dioxido-2-(4-bromobutyl)-5-chloro-1,2-benzisothiazol-3(2H)-one (3.54 g, 10 mmol.) and triethylamine (1.4 mL, 10 mmol.) and allowed to stir at 50° C. under an inert atmosphere for three hours or until reaction was complete. The cooled solution was diluted with EtOAc and washed with NaHCO3 /Na2CO3 solutions, water (3×), and the organic layer dried (Na2SO4), filtered and the solvent evaporated to give 1,1-dioxido-2-(4-(4-(5-fluoro-3-(2,2,2-trifluoroethyl)-2-oxo-1-benzimidazolinyl)piperidin-1-yl)butyl)-5-chloro-1,2-benzisothiazol-3(2H)-one as a viscous oil. This material was dissolved in EtOAc (50 mL) and excess HCl gas/EtOAc was added to give an immediate copious white precipitate which was gently digested in the warmed EtOAc to give the crystalline HCl salt of Compound A, mp: 255-257 ° C. Analysis calculated for C25H25ClF4N4O4S.HCl: C, 48.00; H, 4.19; N, 8.96; found: C, 47.96; H, 4.17; N, 8.93. The NMR was consistent with structure.

Workup

  1. washwashed with NaHCO3 /Na2CO3 solutions, water (3×)
  2. dry with materialthe organic layer dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-d8df4e7c61bf43d0ad9da60a3c8d45e7
Source dataset
uspto-grants-1999_09
Patent number
US05952351

Reaction notes

Loading…