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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2192277Generated: October 31, 2026

Diisopropylethylamine → N-(3-(3-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-6-yl)phenyl)-3-morpholino-5-(trifluoromethyl)benzamide

https://huagongshe.com/reaction/2192277

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantSodium BicarbonateHCID 516892—
ReactantMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
Reactant6-(6-(3-aminophenyl)-3-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amineHCID 50992002—
Reactant3-Morpholino-5-(trifluoromethyl)benzoateHCID 86651380—
SolventTetrahydrofuranHCID 8028—
ProductN-(3-(3-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-6-yl)phenyl)-3-morpholino-5-(trifluoromethyl)benzamideHCID 50992088—

Reaction Steps

HATU (100 mg, 0.260 mmol) was added to a mixture solution of 3-morpholino-5-(trifluoromethyl)benzoate (54 mg, 0.195 mmol), 6-(6-(3-aminophenyl)-3-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (55 mg, 0.130 mmol) and DIPEA (45 μL, 0.26 mmol) in THF (2 mL) at room temperature. 12 hours later, the mixture was added to saturated sodium bicarbonate aqueous solution and then extracted with methylene chloride. The collected organic layer was washed with brine and then concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (preparative HPLC). The target compound was obtained as yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08329708B2
Source datasetuspto-grants-2012_12
ORD IDord-54cb49254a1c4ccab06db7da91fc5c19
Source noteuspto-grants-2012_12