Benzenesulfonyl chloride → HCID 11772625, compound

HRID 2242208Notes

Reaction equation

HRID 2242208 reaction equation
[CH3:1][N:2]([CH3:16])[CH:3]1[CH2:15][C:7]2[C:8]3[CH:9]=[CH:10][NH:11][C:12]=3[CH:13]=[CH:14][C:6]=2[CH2:5][CH2:4]1.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC([O-])(C)C.[K+]>C1COCC1>[CH3:1][N:2]([CH3:16])[CH:3]1[CH2:15][C:7]2[C:8]3[CH:9]=[CH:10][N:11]([S:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:25])=[O:24])[C:12]=3[CH:13]=[CH:14][C:6]=2[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 129503N,N-Dimethyl-6,7,8,9-tetrahydro-3H-benzo[e]indol-8-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 11772625HCID 11772625, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-dimethyl-6,7,8,9-tetrahydro-3H-benzo[e]indol-8-amine (32 mg, 0.2 mmol) in THF is treated with benzenesulfonyl chloride (29.1 mg, 0.22 mmol) followed by KOtBu (19.8 mg, 0.22 mmol), stirred at room temperature for 18 h and concentrated in vacuo. The resultant residue is dissolved in a mixture of DMSO, methanol and water and purified by Gilson preparative HPLC1 to give the title compound, [M+H] 369, retention time (RT) 2.067 minutes. 1Gilson Preparative HPLC conditions: Gilson Preparative HPLC system; YMC Pro C18, 20 mm×50 mm ID, 5 uM column; 2 mL injection; Solvent A: 0.02% TFA/water; Solvent B:0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 2 min: 95% A; 14 min: 10% A, 15 min: 10% A, 16 min: 95% A; Flow rate 22.5 mL/min; Detection: 254 nm DAD.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in a mixture of DMSO, methanol and water
  3. custompurified by Gilson preparative HPLC1

Sources & evidence

ORD record
ord-2d0ea00f4d0349bd901e1c9a8030b7d4
Source dataset
uspto-grants-2010_03
Patent number
US07671079B2

Reaction notes

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