Tetrahydrofuran → Tert-butyl 2-((2-carbamoyl-6-(trifluoromethyl)quinolin-4-yl)amino)acetate

HRID 1896880Notes

Reaction equation

[C:1]([C:3]1[CH:12]=[C:11]([NH:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:22]([F:25])([F:24])[F:23])[CH:9]=2)[N:4]=1)#[N:2].C1C[O:29]CC1>CCO>[C:1]([C:3]1[CH:12]=[C:11]([NH:13][CH2:14][C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:22]([F:25])([F:24])[F:23])[CH:9]=2)[N:4]=1)(=[O:29])[NH2:2]

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of tert-butyl 2-((2-cyano-6-(trifluoromethyl)quinolin-4-yl)amino)acetate (329 mg, 0.94 mmol) from above step A, in EtOH (3 mL) water (600 uL) and THF (5 mL) was added hydrido(dimethylphosphinous acid-kp)[hydrogen bis(dimethylphosphinito-kp)]platinum(ii) (80 mg, 0.18 mmol) and stirred at 75° C. for 3 h. The mixture was filtered to remove the white solid that had formed and the filtrate was evaporated under vacuum. The residue was purified by silica column chromatography to give the title compound.

Workup

filtrationThe mixture was filtered
customto remove the white solid that
customhad formed
customthe filtrate was evaporated under vacuum
customThe residue was purified by silica column chromatography

Sources & evidence

ORD record: ord-142ee245df514d998c7cf1773e5809cc
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518969B2

Reaction notes

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