1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 51000688, compound

Participants

Reaction Steps

To a solution of 2-(phenylamino)acetic acid (37 mg, 0.25 mmol), EDCI (53 mg, 0.275 mmol), and HOBt (37 mg, 0.275 mmol) in DMF (1 mL) was DIEA (1.7 mL, 1.3 mg, 1.0 mmol) and 1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-amine (54 mg, 0.25 mmol). The solution was stirred at rt for several hours, diluted with water and EtOAc (1:1, 10 mL). The organic phase was separated, washed with brine, dried (Na2SO4) and concentrated in vacuo to afford a residue which was purified by reverse phase chromatography C 18 column and 10% acetonitrile/water containing 0.1% TFA to afford example 2. 1H NMR (400 MHz, DMSO-d6) δ 12.67 (s, 1H), 8.35 (s, 1H), 8.06 (d, J=6.8 Hz, 1H), 7.44 (s, 1H), 7.03˜7.70 (m, 3H), 6.52˜6.58 (m, 3H), 4.37 (d, J=12.7 Hz, 1H), 4.25 (d, J=12.2 Hz, 1H), 3.84 (s, 1H), 3.60 (m, 2H), 3.46 (m, 1H), 3.36 (m 1H), 1.87 (m, 2H), 1.61 (m, 2H). EIMS (m/z): calcd. for C19H22N6O (M++1) 351.2. found 351.2.

Provenance & Evidence