1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-{4-[(4-Hydroxypiperidin-1-yl)methyl]benzyl}-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-methylfuran-3-carboxamide

HRID 469039노트

반응식

HRID 469039 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.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.Cl.[CH3:57][NH:58][CH2:59][C:60]1[CH:73]=[CH:72][C:63]([CH2:64][N:65]2[CH2:70][CH2:69][CH:68]([OH:71])[CH2:67][CH2:66]2)=[CH:62][CH:61]=1>C(Cl)Cl.O>[OH:71][CH:68]1[CH2:69][CH2:70][N:65]([CH2:64][C:63]2[CH:72]=[CH:73][C:60]([CH2:59][N:58]([CH3:57])[C:21]([C:18]3[CH:17]=[C:16]([CH2:15][N:13]([S:10]([C:6]4[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[CH3:24])(=[O:11])=[O:12])[CH3:14])[O:20][CH:19]=3)=[O:22])=[CH:61][CH:62]=2)[CH2:66][CH2:67]1

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acidHCID 672169401-{4-[(Methylamino)methyl]benzyl}piperidin-4-ol dihydrochloride

생성물 1

HCID 58393083N-{4-[(4-Hydroxypiperidin-1-yl)methyl]benzyl}-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-methylfuran-3-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (30 mg, 0.085 mmol) was dissolved in DCM (10 mL) and EDCI (27 mg, 0.11 mmol), HOBt (17 mg, 0.127 mmol) and DIPEA (0.03 mL, 0.17 mmol) were added. The resulting solution was stirred for 5 min prior to the addition of 1-{4-[(methylamino)methyl]benzyl}piperidin-4-ol dihydrochloride (28 mg, 0.102 mmol) and stirred at ambient temperature for 16 h. The reaction was diluted with water (5 mL) and extracted with EtOAc (2×15 mL). The combined organic extracts were washed with water (2×5 mL) and brine (5 mL), dried over Na2SO4, and concentrated in vacuo. The resulting residue was purified by FCC eluting with 5% MeOH in DCM to afford the title compound.

후처리

  1. stirringstirred at ambient temperature for 16 h
  2. extractionextracted with EtOAc (2×15 mL)
  3. washThe combined organic extracts were washed with water (2×5 mL) and brine (5 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by FCC
  7. washeluting with 5% MeOH in DCM

출처 및 근거

ORD 기록
ord-bb628e7eef5f4750816a0332b27be216
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623859B2

반응 노트

불러오는 중…