HCID 66599464, 화합물 → HCID 66605740, 화합물

HRID 2410855노트

반응식

HRID 2410855 반응식
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

참가 물질

4

반응물 1

HCID 66599464HCID 66599464, 화합물

생성물 1

HCID 66605740HCID 66605740, 화합물수율 37%

시약·촉매·용매 2

HCID 62406Trifluoromethanesulfonic acid촉매2회HCID 6422Trifluoroacetic acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8b4b0be6ba77434192cf682a6c96572a
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815840B2

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