Sodium Hydroxide → [2-(5-{1-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanol

HRID 1802897Notes

Reaction equation

[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][C:4]([CH:9]([CH2:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[C:10](=O)[CH2:11][CH2:12][C:13]([C:15]2[S:16][C:17]([CH2:20][O:21]C3CCCCO3)=[CH:18][N:19]=2)=O)=[N:3]1.C([O-])(=O)C.[NH4+:40].[OH-].[Na+]>C(O)(=O)C>[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][C:4]([CH:9]([C:10]2[NH:40][C:13]([C:15]3[S:16][C:17]([CH2:20][OH:21])=[CH:18][N:19]=3)=[CH:12][CH:11]=2)[CH2:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[N:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-6-(tetrahydro-2H-pyran-4-yl)-1-{5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazol-2-yl}hexane-1,4-dione (0.65 g), ammonium acetate (0.46 g) and acetic acid (6 mL) was stirred at 100° C. for 1 hr. The reaction mixture was neutralized with 8N aqueous sodium hydroxide solution, 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 basic silica gel column chromatography to give the title compound (0.40 g, yield 80%) as a yellow amorphous solid from the fraction eluted with tetrahydrofuran-hexane (3:1, volume ratio). MS: 419 (MH+).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-19c2123ef53643e09b023d0e1ddd2c37
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349886B2

Reaction notes

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