3-Furanol, tetrahydro- → HCID 86721273, compound

HRID 1750430Notes

Reaction equation

HRID 1750430 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[CH:10][C:9]=2[C:13]2[S:14][CH:15]=[C:16]([CH2:18][C:19]([NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:20])[N:17]=2)=[CH:4][CH:3]=1.O[CH:30]1[CH2:34][CH2:33][O:32][CH2:31]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:30]3[CH2:34][CH2:33][O:32][CH2:31]3)[N:11]=[CH:10][C:9]=2[C:13]2[S:14][CH:15]=[C:16]([CH2:18][C:19]([NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:20])[N:17]=2)=[CH:4][CH:3]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]3[S:14][CH:15]=[C:16]([CH2:18][C:19]([NH:21][CH2:22][CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[O:20])[N:17]=3)=[CH:10][N:11]([CH:30]3[CH2:34][CH2:33][O:32][CH2:31]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

10

Reactant 4

HCID 99603-Furanol, tetrahydro-HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86721270HCID 86721270, compound

Product 2

HCID 86721273HCID 86721273, compoundHCID 90184522HCID 90184522, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixed solution of 2-{2-[5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}-N-(tetrahydro-2H-pyran-4-ylmethyl)acetamide (32.0 mg, 80 μmol) and 3-hydroxytetrahydrofuran (14 mg, 160 μmol) in THF (500 μL) and toluene (500 μL) were added DIAD (31.1 μL, 160 μmol) and triphenylphosphine (42.0 mg, 160 μmol), and the mixture was stirred at 80° C. for 14 hr. To the reaction mixture were added water and ethyl acetate, and the mixture was stirred for 10 min. The organic layer was filtered with a Top-Phase Separation Filter Tube. The filtrate was concentrated. The residue was purified by preparative HPLC to give a mixture (1:3, mol/mol) of a racemic title compound and racemic 2-{2-[3-(4-fluorophenyl)-1-(tetrahydrofuran-3-yl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}-N-(tetrahydro-2H-pyran-4-ylmethyl)acetamide.

Workup

  1. stirringthe mixture was stirred for 10 min
  2. filtrationThe organic layer was filtered with a Top-Phase Separation
  3. filtrationFilter Tube
  4. concentrationThe filtrate was concentrated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9bf3ef821f3c4455aae8b64eb501f42a
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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