Diisopropylethylamine → [5-(2-Methyl-2H-pyrazol-3-yl)-thiophen-3-yl]-octahydro-quinolin-1-yl-methanone

https://huagongshe.com/reaction/2068627

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	cis-Decahydro-quinoline hydrochloride	HCID 12229428	—
Reactant	5-(1-methyl-1H-pyrazol-5-yl)-3-thiophenecarboxylic acid	HCID 58110326	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	[5-(2-Methyl-2H-pyrazol-3-yl)-thiophen-3-yl]-octahydro-quinolin-1-yl-methanone	HCID 44227723	76.6%

Reaction Steps

5-(2-Methyl-2H-pyrazol-3-yl)-thiophene-3-carboxylic acid (0.084 g, 0.40 mmol) was dissolved in THF (2 mL) then DIPEA (0.22 mL, 1.3 mmol) and cis-decahydro-quinoline hydrochloride (DHQ [CIS-S]) (0.084 g, 0.48 mmol) were added followed by HATU (0.182 g, 0.48 mmol). The resulting mixture was stirred overnight then the mixture was diluted with water and extracted with DCM (×2). The organics were dried over sodium sulfate, filtered and evaporated. The crude material was purified by chromatography on a silica II cartridge, eluting with 50-100% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.101 g). LCMS m/z 330.19 [M+H]+ R.T.=10.43 min (Analytical Method 2).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08299063B2
Source dataset	uspto-grants-2012_10
ORD ID	ord-6177e9f8023b4b799bff23de909fee09
Source note	uspto-grants-2012_10