2-(2-cyclopentyl-1-{3-fluoro-4-[1-methyl-1-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-ethyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid → 2-{2-cyclopentyl-1-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

HRID 1515723노트

반응식

HRID 1515723 반응식
[CH:1]1([CH2:6][CH:7]([C:25]2[NH:36][C:28]3=[N:29][CH:30]=[C:31]([C:33]([OH:35])=[O:34])[CH:32]=[C:27]3[CH:26]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:23])([O:16]C3CCCCO3)[CH3:15])=[C:10]([F:24])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C>[CH:1]1([CH2:6][CH:7]([C:25]2[NH:36][C:28]3=[N:29][CH:30]=[C:31]([C:33]([OH:35])=[O:34])[CH:32]=[C:27]3[CH:26]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])([CH3:23])[CH3:15])=[C:10]([F:24])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

3

반응물 1

HCID 672287672-(2-cyclopentyl-1-{3-fluoro-4-[1-methyl-1-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-ethyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

생성물 1

HCID 532514092-{2-cyclopentyl-1-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid수율 28.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 2-(2-cyclopentyl-1-{3-fluoro-4-[1-methyl-1-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-ethyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (1.5 g, 3.04 mmol) in 95% ethanol (50 mL) was added cupric chloride dihydrate (52 mg, 0.3 mmol) at room temperature. The mixture was refluxed for 3 h and then cooled to room temperature. The resulting mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-{2-cyclopentyl-1-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid (350 mg, 28.1%) as a light yellow solid: LC/MS m/e calcd for C24H27FN2O3 [M+H]+ 411.49, observed 410.9; 1H NMR (400 MHz, CD3OD) δ ppm 8.79 (br. s., 1H), 8.56 (br. s., 1H), 7.53-7.60 (m, 1H), 7.13 (br. s., 1H), 7.02 (d, J=12.1 Hz, 1H), 6.51 (br. s., 1H), 4.19 (br. s., 1H), 2.22 (br. s., 1H), 2.12 (br. s., 1H), 1.61-1.88 (m, 5H), 1.56 (br. s., 6H), 1.51 (br. s., 2H), 1.23 (br. s., 2H).

후처리

  1. temperatureThe mixture was refluxed for 3 h
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification

출처 및 근거

ORD 기록
ord-23a442319293408ca34cc7bff3d22dde
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222416B2

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