Triethylamine → HCID 178458617, compound

HRID 75941Notes

Reaction equation

[F:1][C:2]1[N:9]=[C:8](F)[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[CH:19]([O:22][C:23]1[NH:27][N:26]=[C:25]([NH2:28])[CH:24]=1)([CH3:21])[CH3:20]>C(#N)C.O>[F:1][C:2]1[N:9]=[C:8]([NH:28][C:25]2[CH:24]=[C:23]([O:22][CH:19]([CH3:21])[CH3:20])[NH:27][N:26]=2)[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2,5,6-trifluoronicotinonitrile (3.0 g, 19.0 mmol) and triethylamine (2.5 g, 24.7 mmol) in ACN (30 ml) at 0° C. was added 5-isopropoxy-1H-pyrazol-3-amine (2.95 g, 20.9 mmol) in ACN (15 ml). The reaction was stirred at 0° C. for 1 hour, at which point the reaction was diluted with water (50 ml) and extracted with DCM (2×50 ml). The combined organic fractions were dried over Na2SO4, filtered, and then concentrated. The resulting oil was purified by column chromatography (DCM-MeOH=100:1) to give the title compound (0.48 g, 9%). MS: Calcd.: 279. Found: [M+H]+ 280.

Workup

extractionextracted with DCM (2×50 ml)
dry with materialThe combined organic fractions were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe resulting oil was purified by column chromatography (DCM-MeOH=100:1)

Sources & evidence

ORD record: ord-34fe19abe51f4b648f367a2b04be5fb6
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835465B2

Reaction notes

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