2-Dimethylaminopyridine → 1-[(5-Chlorothien-2-yl)sulfonyl]-3-[2-(dimethylamino)ethyl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 1984537노트

반응식

HRID 1984537 반응식
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].[Cl:16][C:17]1[S:21][C:20]([S:22](Cl)(=[O:24])=[O:23])=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.CN(C1C=CC=CN=1)C>C1COCC1>[Cl:16][C:17]1[S:21][C:20]([S:22]([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:5]([CH2:4][CH2:3][N:2]([CH3:15])[CH3:1])[C:6]2=[O:14])(=[O:24])=[O:23])=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 148946781-[2-(Dimethylamino)ethyl]-1,3-dihydrobenzimidazol-2-one

생성물 1

HCID 114290941-[(5-Chlorothien-2-yl)sulfonyl]-3-[2-(dimethylamino)ethyl]-1,3-dihydro-2H-benzimidazol-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-[2-(dimethylamino)ethyl]-1,3-dihydrobenzimidazol-2-one (20 mg, 0.1 mmol) in THF at room temperature is treated with (5-chlorothien-2-yl)sulfonyl chloride (26 mg, 0.12 mmol) followed by diisopropylethylamine (25 uL, 0.2 mmol) and dimethylaminopyridine (5 mg), stirred at room temperature for 16 hours and concentrated in vacuo. The resultant residue is dissolved in a mixture of dimethylsulfoxide, methanol and water and purified by Gilson1 preparative HPLC to give the title product, 16 mg, [M+H] 386, retention time (RT) 2.83 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.

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in a mixture of dimethylsulfoxide, methanol and water
  3. custompurified by Gilson1 preparative HPLC

출처 및 근거

ORD 기록
ord-b202429ebe3943e18864e1e2ed012ecb
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544701B2

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