Hydrochloric Acid → HCID 67188225, compound

HRID 1695194Notes

Reaction equation

C([Li])CCC.CCCCCC.CO[C:14]([C:16]1[CH:17]=[N:18][N:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=12)=[O:15].Cl.[C:26](#[N:28])[CH3:27]>C1(C)C=CC=CC=1>[O:15]=[C:14]([C:16]1[CH:17]=[N:18][N:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=12)[CH2:27][C:26]#[N:28]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of dry acetonitrile in toluene (0.66 mL, 13 mmol, 5 eq) cooled down to −78° C. under nitrogen, a solution of n-butyllithium in n-hexane (5.2 mL, 13 mmol, 5 eq) was added dropwise. The mixture was left stirring at −78° C. for 20 minutes and then a solution of pyrazolo[1,5-a]pyridine-3-carboxylic acid methyl ester (0.46 g, 2.6 mmol, 1 eq, prepared according to the reported procedure (Anderson et al. Journal of Heterocyclic Chemistry 1981, 18, 1149-1152) in toluene was added and the reaction allowed to reach room temperature. Upon reaction completion, after about 20 minutes, the mixture was cooled down to 0° C. and HCl 2N was added to pH 2. The organic phase was recovered, dried over Na2SO4 and concentrated under reduced pressure, affording the title product which was used without further purification in the following step.

Workup

waitThe mixture was left
additionwas added
customto reach room temperature
customUpon reaction completion
waitafter about 20 minutes
temperaturethe mixture was cooled down to 0° C.
customThe organic phase was recovered
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-bc5c75f8b1a542a2968dee8590f195ae
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163729B2

Reaction notes

Loading…