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

Reaction equation

HRID 1802893 reaction equation
[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]

Participants

7

Reactant 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

Product 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-dioneYield 93%

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 702EthanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-a9ebe54701884199bba3b4bce040e29c
Source dataset
uspto-grants-2013_01
Patent number
US08349886B2

Linked notes

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