Ethylenediamine → HCID 57637387, compound

Temperature

70 °C

A portion of this mixture of 5-(3-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-thieno[3,2-c]pyrazole and 5-(3-methoxy-phenyl)-2-(2-trimethylsilanyl-ethoxymethyl)-2H-thieno[3,2-c]pyrazole (4.41 g, 12.2 mmol) and ethylenediamine (2.50 mL, 37.0 mmol) at room temperature under nitrogen was added tetrabutylammonium fluoride (61.0 mL of a 1 M tetrahydrofuran solution, 61.0 mmol) and the resulting solution heated at 70° C. After 21.5 hours, the reaction was cooled to room temperature and the solvent removed in vacuo. Water (150 mL) was added to the residue and the aqueous mixture extracted twice with ethyl acetate (100 mL). The combined extracts were washed with water (75 mL) and brine (75 mL) successively, dried over magnesium sulfate, and concentrated to give 5-(3-methoxy-phenyl)-1H-thieno[3,2-c]pyrazole [2.47 g, 87%, Intermediate (53)] as an off-white solid: TLC Rf 0.45 (silica, ethyl acetate); LC/MS: 231.0 (M+H), RT=3.20 minutes; 1H NMR (300 Mhz, CDCl3) δ 10.65 (br s, 1H), 7.78 (s, 1H), 7.32 (m, 1H), 7.25-7.21 (m, 2H), 7.16 (m, 1H), 6.89 (m, 1H), 3.86 (s, 3H).

1. temperaturethe reaction was cooled to room temperature
2. customthe solvent removed in vacuo
3. additionWater (150 mL) was added to the residue
4. extractionthe aqueous mixture extracted twice with ethyl acetate (100 mL)
5. washThe combined extracts were washed with water (75 mL) and brine (75 mL) successively
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated

ORD record

ord-779a7792b811400abb91bc5798d82d15

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928231B2