1,1'-Carbonyldiimidazole → N-[4-(4,5-dihydro-1H-imidazol-2-yl)benzyl]-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-methylfuran-3-carboxamide

HRID 469007노트

반응식

HRID 469007 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][CH:19]=[C:18]([C:21](O)=[O:22])[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:37]1[CH2:41][CH2:40][N:39]=[C:38]1[C:42]1[CH:47]=[CH:46][C:45]([CH2:48][NH:49][CH3:50])=[CH:44][CH:43]=1.CCN(C(C)C)C(C)C>ClCCCl.CN(C=O)C>[NH:39]1[CH2:40][CH2:41][N:37]=[C:38]1[C:42]1[CH:43]=[CH:44][C:45]([CH2:48][N:49]([CH3:50])[C:21]([C:18]2[CH:17]=[C:16]([CH2:15][N:13]([S:10]([C:6]3[C:5]([CH3:24])=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=3[CH3:9])(=[O:11])=[O:12])[CH3:14])[O:20][CH:19]=2)=[O:22])=[CH:46][CH:47]=1

참가 물질

7

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 552648631-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamine2회HCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

생성물 1

HCID 58393008N-[4-(4,5-dihydro-1H-imidazol-2-yl)benzyl]-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-methylfuran-3-carboxamide

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매

실험 절차

5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (30 mg, 0.09 mmol) was dissolved in DCE (2 mL) and CDI (30 mg, 0.18 mmol) added. The reaction was stirred at room temperature until complete as determined by LCMS. 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamine (32 mg, 0.17 mmol) and DIPEA (0.032 mL, 0.18 mmol) was added and the reaction stirred for 3 days at ambient temperature. A further 32 mg 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamine was added, followed by DMF (0.5 mL) and the reaction was stirred for 18 h. The reaction was washed with saturated aqueous NH4Cl (3×5 mL) and the organic layer dried over MgSO4, shaken with PL-MIA and Ambersep resins, and concentrated. A portion of the crude product was purified using prep method C.

후처리

  1. stirringthe reaction stirred for 3 days at ambient temperature
  2. stirringthe reaction was stirred for 18 h
  3. washThe reaction was washed with saturated aqueous NH4Cl (3×5 mL)
  4. dry with materialthe organic layer dried over MgSO4
  5. stirringshaken with PL-MIA and Ambersep resins
  6. concentrationconcentrated
  7. customA portion of the crude product was purified

출처 및 근거

ORD 기록
ord-ba1bab81392d46a7a44b8b705ed298e5
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623859B2

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