Triethylamine → Benzothiophene-2-sulfonic acid [1-(4-chloroquinolin-6-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide

HRID 651641Notes

Reaction equation

HRID 651641 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[C:12]3[Cl:19])[C:4]1=[O:20].C(N(CC)CC)C.[S:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[CH:30]=[C:29]1[S:37](Cl)(=[O:39])=[O:38]>CC#N>[Cl:19][C:12]1[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([CH2:8][N:5]3[CH2:6][CH2:7][C@H:3]([NH:2][S:37]([C:29]4[S:28][C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=5[CH:30]=4)(=[O:38])=[O:39])[C:4]3=[O:20])[CH:10]=2)[N:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27763331-Benzothiophene-2-sulfonyl chlorideHCID 206807203-(S)-Amino-1-(4-Chloroquinolin-6-ylmethyl)-pyrrolidin-2-one hydrochloride

Product 1

HCID 54330909Benzothiophene-2-sulfonic acid [1-(4-chloroquinolin-6-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amideYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(S)-Amino-1-(4-chloroquinolin-6-ylmethyl)-pyrrolidin-2-one hydrochloride (0.12 g, 0.38 mmol) is suspended in 15 mL CH3CN. To this solution is added triethylamine (110 mL, 0.79 mmol) followed by benzothiophene-2-sulfonyl chloride (0.094 g, 0.40 mmol). The mixture is stirred overnight at room temperature, subjected to aqueous work up then concentrated to dryness. The crude product is purified by column chromatography eluting with 2-10% MeOH/CH2Cl2 to give the title compound (0.11 g, 0.23 mmol) as an off-white solid.

Workup

  1. concentrationup then concentrated to dryness
  2. customThe crude product is purified by column chromatography
  3. washeluting with 2-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-6c55f5a64b05415cabbcf64be3d3278c
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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