N,N-Dimethylethylenediamine → HCID 71230972, compound

To a suspension of Intermediate 12b (1 g, 3.87 mmol) in DCM (20 ml) was added COMU (1.891 g, 4.26 mmol) and DIPEA (0.812 ml, 4.65 mmol). The yellow solution was stirred for 2 min at rt and turned red. 2-Dimethylaminoethylamine (0.518 ml, 4.65 mmol) was added and the reaction mixture was stirred at reflux for 1 hr. After cooling to rt, the mixture was washed with water, saturated aqueous NH4Cl and extrated with EtOAc. The organic layer was dried over Na2SO4 and the solvent was removed in vacuo. The crude product was purified by flash chromatography (ISCO CombiFlash Rf, 120 g silicagel; A=dichloromethane, B=DCM:7N NH3 in MeOH (9:1), 2% hold for 5 min, gradient to 50% B over 15 min). Fractions containing the product where combined to yield 1.355 g. The final product (1.015 g) was obtained after crystallisation from heptane as a white solid.

1. stirringthe reaction mixture was stirred
2. temperatureat reflux for 1 hr
3. temperatureAfter cooling to rt
4. washthe mixture was washed with water, saturated aqueous NH4Cl
5. dry with materialThe organic layer was dried over Na2SO4
6. customthe solvent was removed in vacuo
7. customThe crude product was purified by flash chromatography (ISCO CombiFlash Rf, 120 g silicagel
8. waitA=dichloromethane, B=DCM:7N NH3 in MeOH (9:1), 2% hold for 5 min
9. waitgradient to 50% B over 15 min)
10. additionFractions containing the product where
11. customto yield 1.355 g

ORD record

ord-939cd4ccdd5a47ceae382044c987c40e

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056843B2