HCID 11643282, compound → N-[2-(1-benzhydryl-5-chloro-1H-indol-2-yl)ethyl]-1-(3,4-dichlorophenyl)methanesulfonamide

HRID 1663610Notes

Reaction equation

HRID 1663610 reaction equation
C(OC([N:8]([CH2:21][CH2:22][C:23]#[C:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[NH:32][CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[S:9]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)(=[O:11])=[O:10])=O)(C)(C)C>[Cu]I.CN(C)C(=O)C>[CH:33]([N:32]1[C:26]2[C:25](=[CH:30][C:29]([Cl:31])=[CH:28][CH:27]=2)[CH:24]=[C:23]1[CH2:22][CH2:21][NH:8][S:9]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)(=[O:11])=[O:10])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

4

Reactant 1

HCID 11643282HCID 11643282, compound

Product 1

HCID 11204051N-[2-(1-benzhydryl-5-chloro-1H-indol-2-yl)ethyl]-1-(3,4-dichlorophenyl)methanesulfonamideYield 99%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
150 °C

Procedure

A solution of N-t-butoxycarbonyl-N-{4-[2-(benzhydryl-amino)-5-chloro-phenyl]-but-3-ynyl}-C-(3,4-dichlorophenyl)-methanesulfonamide (400 g, 0.585 mol) and N,N-dimethylacetamide (800 mL) was added slowly over 1 h to a hot (150° C.), stirred mixture of copper (I) iodide (12.2 g, 0.064 mol) and N,N-dimethylacetamide (740 mL). The reaction mixture was stirred and maintained at 150° C. for an additional 2 h. The reaction mixture was cooled to 40° C. The mixture was filtered through a celite pad and the pad was washed with IPA (2×100 mL). An additional charge of IPA (1400 mL) was added to the filtrate. The mixture was stirred and warmed to 60° C. Water (2.2 L) was added to the mixture over 30 m, maintaining an internal temperature of 55-60° C. The mixture was held at 60° C. for 30 m, then it was cooled to 5° C. The solid product was collected by filtration and the cake was washed with cold IPA/water (3/2 v/v, 2×200 mL). The solid was vacuum dried at <50° C. to give N-[2-(1-benzhydryl-5-chloro-1H-indol-2-yl)-ethyl]-C-(3,4-dichloro-phenyl)-methanesulfonamide (338 g, 99%) with 98% purity (as determined by HPLC).

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureThe reaction mixture was cooled to 40° C
  3. filtrationThe mixture was filtered through a celite pad
  4. washthe pad was washed with IPA (2×100 mL)
  5. additionAn additional charge of IPA (1400 mL)
  6. additionwas added to the filtrate
  7. stirringThe mixture was stirred
  8. temperaturewarmed to 60° C
  9. additionWater (2.2 L) was added to the mixture over 30 m
  10. temperaturemaintaining an internal temperature of 55-60° C
  11. customwas held at 60° C. for 30 m
  12. temperatureit was cooled to 5° C
  13. filtrationThe solid product was collected by filtration
  14. washthe cake was washed with cold IPA/water (3/2 v/v, 2×200 mL)
  15. customdried at <50° C.

Sources & evidence

ORD record
ord-0248f0bd8f154f62bb5d0dfbd5251a0f
Source dataset
uspto-grants-2011_10
Patent number
US08034960B2

Reaction notes

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