3-Hydroxy-2,2-dimethylpropionic acid → 6-[1-(3-Hydroxy-2,2-dimethylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-1,3-benzothiazol-6-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

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Reaction Steps

To a mixture of benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine trihydrochloride (50.0 mg, 0.11 mmol) in DMF (3 mL) was added 2,2-dimethyl-3-hydroxypropionic acid (150 mg, 1.3 mmol), TBTU (42.0 mg, 0.13 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.50 mmol). The reaction mixture stirred at rt for 16 h. The mixture was concentrated in vacuo and purified via MDP, which afforded the title compound as yellow solid. MS (ES+): m/z: 448.96 (100) [MH+]. HPLC: tr=2.35 min (ZQ2000: polar—5 min). 1H NMR (400 MHz, DMSO-d6): δ=1.20 (s, 6H), 3.19 (s, 1H), 3.46 (s, 2H), 3.79-3.81 (m, 2H), 4.21 (s, 2H), 4.59 (bs, 1H), 6.43 (s, 1H), 6.84 (d, J=1.6 Hz, 1H), 7.87 (dd, J=1.6, 8.8 Hz, 1H), 8.03 (d, J=8.8 Hz, 1H), 8.34 (s, 1H), 8.91 (d, J=2.0 Hz, 1H), 9.23 (s, 1H), 9.62 (s, 1H), 12.03 (s, 1H).

Provenance & Evidence