2-(Dimethylamino)ethanol → HCID 118037497, compound

2-(dimethylamino)ethanol (0.293 ml, 2.92 mmol) was treated at room temperature with KHMDS (1 M in THF, 2.19 ml, 2.19 mmol). The reaction mixture was stirred for 2 min and then added to a solution of 6-amino-4-fluoronicotinonitrile (intermediate 21, 100 mg, 0.729 mmol) in THF (2 ml). The resulting dark brown solution was stirred at room temperature for 60 min, quenched with sat. aq. NH4Cl, directly absorbed on isolate and dried under vacuum. The crude material was purified by reverse phase chromatography (13 g C18 cartridge, 0.1% TFA in water/acetonitrile 100:0 to 0:100). The product containing fractions were concentrated. The residue was treated with a small amount sat. aq. NaHCO3 and NaCl (s) and extracted with CH2Cl2 (5×). The combined organic layers were dried over Na2SO4 and concentrated to give the title compound as a white solid. (UPLC-MS 3) tR 0.45 min; ESI-MS 207.2 [M+H]+.

1. stirringThe resulting dark brown solution was stirred at room temperature for 60 min
2. customquenched with sat. aq. NH4Cl
3. customdirectly absorbed
4. customon isolate
5. customdried under vacuum
6. customThe crude material was purified by reverse phase chromatography (13 g C18 cartridge, 0.1% TFA in water/acetonitrile 100:0 to 0:100)
7. additionThe product containing fractions
8. concentrationwere concentrated
9. additionThe residue was treated with a small amount sat. aq. NaHCO3 and NaCl (s)
10. extractionextracted with CH2Cl2 (5×)
11. dry with materialThe combined organic layers were dried over Na2SO4
12. concentrationconcentrated

ORD record

ord-a81bd62bb7b34b7d9a8efc29e8676167

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266883B2