Benzenesulfonyl chloride → HCID 11371056, compound

HRID 1823963Notes

Reaction equation

HRID 1823963 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][C:6]1[C:7]2[CH:13]=[CH:12][S:11][C:8]=2[NH:9][CH:10]=1)[CH3:3].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC([O-])(C)C.[K+]>C1COCC1>[CH3:1][N:2]([CH2:4][CH2:5][C:6]1[C:7]2[CH:13]=[CH:12][S:11][C:8]=2[N:9]([S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])[CH:10]=1)[CH3:3]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 10058473HCID 10058473, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11371056HCID 11371056, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixtue of N,N-dimethyl-2-(6H-thieno[2,3-b]pyrrol-4-yl)ethylamine (0.2 mmol), benzenesulfonyl chloride (0.22 mmol) and KOt-Bu (0.22 mmol) in THF is shaken at ambient temperatures for 8 h and concentrated in vacuo. The resultant residue is dissolved in a mixture of DMSO, methanol and water and purified by preparative HPLC1 to afford the title product, [M+H] 335, retention time (RT) 1.42 min. 1 Gilson 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 preparative HPLC1

Sources & evidence

ORD record
ord-998a0dcbe4914867acd400c728afee87
Source dataset
uspto-grants-2006_05
Patent number
US07041695B2

Reaction notes

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