1,1'-Carbonyldiimidazole → 2,6-dichloro-N-methyl-N-[(4-{[4-(2-pyridin-4-ylethyl)piperazin-1-yl]carbonyl}furan-2-yl)methyl]benzenesulfonamide

HRID 468996

반응식

HRID 468996 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([N:12]([CH2:14][C:15]1[O:19][CH:18]=[C:17]([C:20](O)=[O:21])[CH:16]=1)[CH3:13])(=[O:11])=[O:10].C1N=CN(C(N2C=NC=C2)=O)C=1.[N:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][N:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[CH:37][CH:36]=1>ClCCCl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9]([N:12]([CH3:13])[CH2:14][C:15]1[O:19][CH:18]=[C:17]([C:20]([N:46]2[CH2:47][CH2:48][N:43]([CH2:42][CH2:41][C:38]3[CH:37]=[CH:36][N:35]=[CH:40][CH:39]=3)[CH2:44][CH2:45]2)=[O:21])[CH:16]=1)(=[O:10])=[O:11]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 5586851-[2-(4-Pyridinyl)ethyl]piperazineHCID 583932575-({[(2,6-Dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

생성물 1

HCID 461754542,6-dichloro-N-methyl-N-[(4-{[4-(2-pyridin-4-ylethyl)piperazin-1-yl]carbonyl}furan-2-yl)methyl]benzenesulfonamide

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

5-({[(2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (465 mg, 1.3 mmol) was dissolved in DCE (40 mL) and CDI (422 mg, 2.6 mmol) was added. The reaction was stirred for 1 h. 4 mL of activated acid solution in DCE was added to a vial containing 1-[2-(pyridin-4-yl)ethyl]piperazine (50 mg, 0.261 mmol). The reaction was stirred at ambient temperature for 3 days, then washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and shaken with PL-MIA and Ambersep resins, then filtered. The solvent was removed in vacuo and a portion of the crude product purified using prep method B.

후처리

  1. stirringThe reaction was stirred at ambient temperature for 3 days
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. stirringshaken with PL-MIA and Ambersep resins
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customa portion of the crude product purified

출처 및 근거

ORD 기록
ord-3bc8f6fcc1b84f2bb82de17283ec48af
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623859B2

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