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 469039ノート

反応式

HRID 469039 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bb628e7eef5f4750816a0332b27be216
出典データセット
uspto-grants-2014_01
特許番号
US08623859B2

反応ノート

読み込み中…