N-Acetyl-beta-alanine → 3-acetylamino-N-(1-benzenesulfonyl-4-cyclohexylamino-1H-pyrrolo[2,3-b]pyridin-5-yl)-propionamide

温度

25 °C

3-Acetylaminopropionic acid (0.089 g, 0.675 mmol), HATU (0.256 g, 0.675 mmol), and diisopropylethylamine (0.141 ml, 0.840 mmol) were added sequentially to a solution of 1-benzenesulfonyl-N-4-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (0.250 g, 0.675 mmol) in CH2Cl2 (15 ml) at 25° C. The reaction mixture was stirred for 18 h at 25° C., then was partitioned between half-saturated NaHCO3 (100 ml) and EtOAc (2×125 ml). The combined organic layers were dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with EtOAc (10 ml) to give a solid which was collected by filtration, washed with Et2O (10 ml), and air-dried to give 3-acetylamino-N-(1-benzenesulfonyl-4-cyclohexylamino-1H-pyrrolo[2,3-b]pyridin-5-yl)-propionamide as an off-white solid (0.183 g, 56%). LCMS (Method G, ESI): RT=0.82 min, m+H=484.3. This material was used in the next step below without additional purification or characterization.

1. customwas partitioned between half-saturated NaHCO3 (100 ml) and EtOAc (2×125 ml)
2. dry with materialThe combined organic layers were dried over MgSO4
3. filtrationfiltered
4. concentrationthe filtrate was concentrated under reduced pressure
5. customThe residue was triturated with EtOAc (10 ml)
6. customto give a solid which
7. filtrationwas collected by filtration
8. washwashed with Et2O (10 ml)
9. customair-dried

ORDレコード

ord-75e50a223085478c8671d71c54dcdc38

出典データセット

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08461328B2