Sodium Hydroxide → 4-Ethyl-1-(5-(2-(3-ethylureido)-7-propionylbenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylic acid

To a solution of ethyl 4-ethyl-1-(5-(2-(3-ethylureido)-7-propionylbenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate (0.025 g, 0.046 mmol) in EtOH (5 mL) was added an aqueous solution (1 mL) of NaOH (0.0092 g, 0.232 mmol) and the mixture stirred overnight at 80° C. After reaction completion (by TLC), the EtOH was evaporated under reduced pressure, water (10 mL) was added to the residue and extracted with EtOAc (3×25 mL) and the organic layers discarded. The aqueous layer was acidified to pH 4-5 with 1N HCl, extracted with EtOAc (3×25 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4, filtered then concentrated under reduced pressure. The residue was purified by preparative TLC (5% MeOH in DCM) to obtain Compound 207 as white solid (0.007 g, 30%). 1H NMR (DMSO-d6): δ 10.82 (br s, 1H), 8.86 (s, 2H), 8.23 (s, 1H), 8.14 (s, 1H), 6.95 (br s, 1H), 4.46 (m, 2H), 3.36 (m, 2H), 3.13-3.24 (m, 4H), 2.08 (m, 2H), 1.51-1.53 (m, 2H), 1.32 (m, 2H), 1.16 (t, J=7.2 Hz, 3H), 1.10 (t, J=7.2 Hz, 3H) and 0.81 (t, J=7.2 Hz, 3H). MS: 511.24 [M+H]+.

1. customAfter reaction completion (by TLC)
2. customthe EtOH was evaporated under reduced pressure, water (10 mL)
3. additionwas added to the residue
4. extractionextracted with EtOAc (3×25 mL)
5. extractionextracted with EtOAc (3×25 mL)
6. washthe combined organic layers washed with brine
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationthen concentrated under reduced pressure
10. customThe residue was purified by preparative TLC (5% MeOH in DCM)

ORD record

ord-63a5ff0612944354aa9013015494a40e

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181234B2