Dimethylamine → HCID 178430912, compound

To a mixture of 4-methyl-1H-pyrazole-3-carboxylic acid (1.00 g, 7.93 mmol), HOBT (1.07 g, 7.93 mmol) and EDCI (2.27 g, 11.89 mmol) in DMF (10 mL) was added DIEA (2.74 mL, 15.86 mmol). After the mixture was stirred at room temperature for 16 hours, dimethylamine (2M in THF, 11.89 mL, 23.79 mmol) was added. The mixture was stirred at room temperature for 3 hours, then partitioned between EtOAc (300 mL) and water (30 mL). The organics was washed with brine (3×30 mL) and the combined aqueous material was back extracted with EtOAc (2×50 mL). All organic extracts were combined, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% MeOH in CH2Cl2) to obtain the title compound as a brown oil (1.1 g, 92%). m/z (ES+) 154 (M+H)+.

1. stirringThe mixture was stirred at room temperature for 3 hours
2. custompartitioned between EtOAc (300 mL) and water (30 mL)
3. washThe organics was washed with brine (3×30 mL)
4. extractionthe combined aqueous material was back extracted with EtOAc (2×50 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (5% MeOH in CH2Cl2)

ORD record

ord-31b8b29a6ac04624b169d29bffbbbc3d

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2