Tetrahydrofuran → HCID 86721199, compound

HRID 1750361Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:11]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[C:14]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][C:29](O)=O)[N:27]=2)[CH:13]=[N:12]1)([CH3:10])([CH3:9])[CH3:8].[CH2:32]1[CH2:36]OCC1>[OH-].[Na+]>[C:7]([N:11]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[C:14]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][CH2:29][N:27]3[CH2:32][CH2:36][S:24][CH2:25][CH2:26]3)[N:27]=2)[CH:13]=[N:12]1)([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of lithium aluminum hydride (4.93 mg, 0.13 mmol) in THF (3 mL) was added 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid (68 mg, 0.15 mmol) at room temperature, and the mixture was stirred at 80° C. for 2 hr. To the reaction mixture was added 1N aqueous sodium hydroxide solution (2 drops), and the mixture was stirred at room temperature for 1 hr. After extraction with ethyl acetate, washing with saturated brine and drying, the solvent was evaporated under reduced pressure. The residue was purified by NH-silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane) to give the title compound (8 mg, 0.019 mmol, 12.15%) as a pale-yellow oil.

Workup

stirringthe mixture was stirred at room temperature for 1 hr
extractionAfter extraction with ethyl acetate
washwashing with saturated brine
customdrying
customthe solvent was evaporated under reduced pressure
customThe residue was purified by NH-silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-dc0502c55536424fbea00ab67663819f
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156837B2

Reaction notes

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