Water → 5-Ethynyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-dimethylcarbamoyl-2-phenyl ethyl)amide

To a solution of 2-(S)-amino-N,N-dimethyl-3-phenylpropionamide hydrochloride (Preparation 8, 0.0135 g, 0.059 mmol) in DMF (anhydrous, 3 mL) was added DIPEA (0.031 mL, 0.177 mmol) then carboxylic acid (Preparation 60, 0.010 g, 0.054 mmol). To the stirred solution was added HOBt.H2O (0.008 g, 0.059 mmol) then, after 10 min, EDCI (0.012 g, 0.065 mmol). The reaction mixture was stirred for 18 h then all volatiles were removed in vacuo. The residue was partitioned between ethyl acetate (30 mL) and water (20 mL). The layers were separated and the aqueous layer extracted with ethyl acetate (3×20 mL). The combined organics were washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in methanol then adsorbed onto silica gel. Purification via flash column chromatography (SiO2, CH2Cl2:MeOH, 19:1, v/v) gave the title compound as an off-white solid. δH (CD3OD): 2.88 (3H, s), 2.89 (3H, s), 3.00–3.23 (2H, m), 3.50 (1H, s), 5.27 (1H, t), 7.10–7.37 (6H, m), 7.86 (1H, s), 8.70 (1H, s). m/z (ES+)=361 [M+H]+; RT=2.65 min.

1. customall volatiles were removed in vacuo
2. customThe residue was partitioned between ethyl acetate (30 mL) and water (20 mL)
3. customThe layers were separated
4. extractionthe aqueous layer extracted with ethyl acetate (3×20 mL)
5. washThe combined organics were washed with brine (30 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. dissolutionThe residue was dissolved in methanol
10. customPurification via flash column chromatography (SiO2, CH2Cl2

ORDレコード

ord-cb13b6af6b7547fe9437a6afc2ada4d5

出典データセット

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07405210B2