HCID 66599464、化合物 → HCID 66605740、化合物

HRID 2410855ノート

反応式

HRID 2410855 の反応式
C([N:8]1[C:16]2[CH:15]=[C:14]([O:17][CH3:18])[CH:13]=[CH:12][C:11]=2[C:10]2[N:19]=[C:20]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:9]1=2)C1C=CC=CC=1>C(O)(C(F)(F)F)=O.FC(F)(F)S(O)(=O)=O>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]2[C:10]3[N:19]=[C:20]([N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:9]=3[NH:8][C:16]=2[CH:15]=1

参加物

4

反応物 1

HCID 66599464HCID 66599464、化合物

生成物 1

HCID 66605740HCID 66605740、化合物収率 37%

試薬・触媒・溶媒 2

HCID 62406Trifluoromethanesulfonic acid触媒2 回HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of methyl 5-benzyl-7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (51 mg, 0.12 mmol) in TFA (2 mL) and two drops of trifluoromethanesulfonic acid was heated at reflux for 30 min. Another two drops of trifluoromethanesulfonic acid was added and heating continued for another 40 min. Preparative HPLC (100×30 mm Luna C18 column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile; gradient of 15 to 100% B over 20 min at 42 mL/min) followed by removal of the solvents afforded methyl 7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (15 mg, 0.044 mmol, 37% yield). MS (ESI) m/z 340.2 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.02 (1H, br. s.), 8.09 (1H, d, J=8.85 Hz), 7.22 (1H, s), 6.89 (1H, s), 6.85 (1H, d, J=8.55 Hz), 4.02 (3H, s), 3.90 (3H, s), 3.53-3.64 (4H, m), 1.69-1.80 (4H, m), 1.56-1.67 (2H, m).

後処理

  1. temperatureat reflux for 30 min
  2. temperatureheating
  3. customPreparative HPLC (100×30 mm Luna C18 column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile; gradient of 15 to 100% B over 20 min at 42 mL/min) followed by removal of the solvents

出典と根拠

ORDレコード
ord-8b4b0be6ba77434192cf682a6c96572a
出典データセット
uspto-grants-2014_08
特許番号
US08815840B2

反応ノート

読み込み中…