Triethylamine → HCID 57992292, compound

HRID 1921237Notes

Reaction equation

HRID 1921237 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].Cl.[F:14][C:15]([F:32])([F:31])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH2:26][CH2:25]3)=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[F:32][C:15]([F:14])([F:31])[C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:26][CH2:25]3)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 67492862HCID 67492862, compound

Product 1

HCID 57992292HCID 57992292, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.25 g of commercially available 4-cyano-benzenesulfonyl chloride were dissolved in 35 ml dichloromethane. Then 760 mg 5-(4-trifluoromethyl-phenyl)-2,3-dihydro-1H-indole hydrochloride were added followed by 2.14 ml triethylamine. The mixture was stirred at room temperature for fifteen minutes. Then 100 ml of dichloromethane were added, the mixture washed with 40 ml water and brine and then dried over MgSO4. The solvent was removed in vacuo. The resulting crude material was purified by reversed phase HPLC to obtain 517 mg of 4-[5-(4-trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile as amorphous lyophilisate.

Workup

  1. washthe mixture washed with 40 ml water and brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customThe resulting crude material was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-5bc245259fb44905bc392a00ebe0befb
Source dataset
uspto-grants-2012_05
Patent number
US08173674B2

Reaction notes

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