Triethylamine → HCID 86753990, compound

HRID 1637706Notes

Reaction equation

HRID 1637706 reaction equation
Cl.[N:2]1([C:8]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=3)[NH:13][CH:12]=2)=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N([CH2:27][CH3:28])CC)C.[C:29]1(C)[C:30]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:32]=C[CH:34]=1>C(Cl)(Cl)Cl>[C:27]1([CH3:28])[CH:32]=[CH:31][C:30]([S:35]([N:5]2[CH2:6][CH2:7][N:2]([C:8]([CH2:10][C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=4)[NH:13][CH:12]=3)=[O:9])[CH2:3][CH2:4]2)(=[O:37])=[O:36])=[CH:29][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 18800608HCID 18800608, compound

Product 1

HCID 86753990HCID 86753990, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 3-(piperazinecarbonyl)methyl-5-cyanoindole hydrochloride (200 mg, 0.66 mmol) and triethylamine (134 mg, 185 μL) in chloroform was added toluenesulfonylchloride (126 mg, 0.66 mmol). After stirring for 18 h at rt under a nitrogen atmosphere, the reaction was quenched with water, extracted with chloroform, washed with 1 N HCl, sat sodium bicarbonate, and brine, dried with sodium sulfate, filtered and concentrated in vacuo to afford 237 mg of product. LRMS (M+H)+ 423.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with chloroform
  3. washwashed with 1 N HCl
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba9a6e7a1f0f49ff849d220b9ea66ec9
Source dataset
uspto-grants-2000_03
Patent number
US06043257

Reaction notes

Loading…