1-Hydroxybenzotriazole → HCID 17144262, compound

To a suspension of p-tolylacetic acid (1.00 g, 6.66 mmol) and 2-amino-5-methylthiazole (0.760 g, 6.66 mmol) in dichloromethane (10 mL) was added at 0° C. under a nitrogen atmosphere 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.40 g, 7.32 mmol), 1-hydroxybenzotriazole (90 mg, 0.67 mmol) and N,N-diisopropyl ethyl amine (1.8 mL, 10 mmol). The ice bath was removed and the resulting solution was stirred for 3 h at ambient temperature. The reaction mixture was diluted with dichloromethane (20 mL) and washed with aqueous sodium carbonate (half-concentrated, 20 mL) and water (20 mL). The aqueous layers were extracted with dichloromethane (20 mL) and the combined organic layers were dried over sodium sulfate. The filtrate was concentrated and the residue was suspended in TBME (20 mL) and filtered. Washing with TBME (10 mL) afforded the title compound (1.48 g, 90%) as a white solid. MS m/e: 247.2 [M+H]+.

1. customThe ice bath was removed
2. additionThe reaction mixture was diluted with dichloromethane (20 mL)
3. washwashed with aqueous sodium carbonate (half-concentrated, 20 mL) and water (20 mL)
4. extractionThe aqueous layers were extracted with dichloromethane (20 mL)
5. dry with materialthe combined organic layers were dried over sodium sulfate
6. concentrationThe filtrate was concentrated
7. filtrationfiltered
8. washWashing with TBME (10 mL)

ORD record

ord-bc4a613d8ca84ac084abfc8657b0bdda

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08133909B2