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

反応式

HRID 1802893 の反応式
[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]

参加物

7

反応物 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

生成物 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-dione収率 93%

試薬・触媒・溶媒 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride触媒HCID 702Ethanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-a9ebe54701884199bba3b4bce040e29c
出典データセット
uspto-grants-2013_01
特許番号
US08349886B2

関連ノート

読み込み中…