2-Phenoxyethanamine → 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid (2-phenoxyethyl)amide

To a solution of 1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (Preparation 32, 50 mg, 0.31 mmol) in DMF (5 mL), was added 2-phenoxyethylamine (44 μL, 0.34 mmol), DIPEA (118 μL, 0.68 mmol) and HOBt (42 mg, 0.31 mmol) sequentially. The reaction mixture was stirred for 5 min prior to the addition of EDCI (42 mg, 0.22 mmol) in one portion. The resulting mixture was stirred for 20 h at rt and partitioned between ethyl acetate (50 mL) and water (20 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×30 mL). The combined organic fractions were washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo to give an oil. Trituration with diethyl ether/isohexane and collection by filtration gave, after air-drying, the title compound as a cream coloured solid. δH (d6 DMSO): 3.48 (2H, m), 4.14 (2H, t), 6.94 (3H, m), 7.17 (1H, dd), 7.28 (3H, m), 7.77 (1H, d), 8.37 (1H, dd), 8.86 (1H, t); m/z (ES+)=282 [M+H]+; RT=2.60 min.

1. stirringThe resulting mixture was stirred for 20 h at rt
2. custompartitioned between ethyl acetate (50 mL) and water (20 mL)
3. customThe layers were separated
4. extractionthe aqueous phase extracted with ethyl acetate (2×30 mL)
5. washThe combined organic fractions were washed with brine (20 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give an oil
10. customTrituration with diethyl ether/isohexane and collection
11. filtrationby filtration
12. customgave
13. customafter air-drying

ORD record

ord-d70bb6229f3d4afd901ace10b922a8cf

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158622B2