Tetrahydrofuran → 1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-5-(4-methoxy-1H-pyrazolo[3,4-b]pyridin-1-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1802893

반응식

HRID 1802893 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[N:9]([CH:12]([CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:13](=[O:16])[CH:14]=[CH2:15])[N:10]=[CH:11][C:4]=12.[OH:24][CH:25]([C:30]1[CH:31]=[CH:32][C:33]([CH:36]=[O:37])=[N:34][CH:35]=1)[C:26]([OH:29])([CH3:28])[CH3:27].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[OH:24][CH:25]([C:30]1[CH:31]=[CH:32][C:33]([C:36](=[O:37])[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([N:9]2[C:5]3=[N:6][CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]3[CH:11]=[N:10]2)[CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:34][CH:35]=1)[C:26]([OH:29])([CH3:27])[CH3:28]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593314885-(1,2-Dihydroxy-2-methylpropyl)pyridine-2-carbaldehydeHCID 673521164-(4-methoxy-1H-pyrazolo[3,4-b]pyridin-1-yl)-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

생성물 1

HCID 673529111-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-5-(4-methoxy-1H-pyrazolo[3,4-b]pyridin-1-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione수율 93%

시약·촉매·용매 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride촉매HCID 702Ethanol용매

실험 절차

A mixture of 4-(4-methoxy-1H-pyrazolo[3,4-b]pyridin-1-yl)-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (178 mg), 5-(1,2-dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde (132 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (18 mg), triethylamine (30 μL), tetrahydrofuran (5 mL) and ethanol (5 mL) was heated under reflux for 3 hr under argon stream. The reaction solution was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to give the title compound (268 mg, yield 93%) as a pale-yellow oil from the fraction eluted with ethyl acetate. MS: 511 (MH+).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr under argon stream
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a9ebe54701884199bba3b4bce040e29c
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349886B2

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