Diisopropylethylamine → HCID 69289368, compound

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	4-(2-METHOXYCARBONYL-ETHYL)-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLIC ACID	HCID 10846813	—
Reactant	1-(Propan-2-yl)piperidin-4-amine dihydrochloride	HCID 17750340	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 69289368	HCID 69289368	40.6%

Reaction Steps

263 mg of (1.17 mmol) 4-(2-methoxycarbonyl-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid were dissolved in DMF (10 mL). 488.4 mg (1.28 mmol) of HATU and DIEA (224 μl) were added and the resulting mixture was stirred for 45 minutes at RT. A solution of 276.3 mg (1.28 mmol) of 1-isopropyl-piperidine-4-ylamine-dihydrochloride and 448 μl of DIEA was added. The reaction mixture was stirred over night after which it was concentrated. The residue was diluted with DCM and washed with a saturated NaHCO3 solution and brine. The organic layer was dried over MgSO4 and concentrated. Preparative HPLC(CH3CN/H2O gradient+0.05% formic acid) gave pure 3-[5-(1-isopropyl-piperidin-4-ylcarbamoyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid methyl ester (166 mg) as a colorless amorphous material. MS (ESI+): m/e=351 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07465806B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-6d6470a8dc5f4e32b5d88017b3cb7564
Source note	uspto-grants-2008_12