Dimethylformamide → HCID 178484485, compound

Participants

Reaction Steps

N,N-Diisopropylethylamine (10.31 μL, 0.05920 mmol) and 6-[(cis-4-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}cyclohexyl)oxy]-2-(trifluoromethyl)pyrimidine-4-carboxylic acid (20.00 mg, 0.02866 mmol) were dissolved in N,N-dimethylformamide (0.53 mL) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (19.60 mg, 0.05154 mmol) in N,N-dimethylformamide (1.00 mL) was added. The reaction mixture was stirred for 10 minutes and dimethylamine hydrochloride (6.09 mg, 0.0747 mmol) was added. The reactions were stirred at 25° C. overnight at which time LCMS analysis showed that the reaction was mostly complete and was purified by LC and evaporated and deprotected as in Example 1 (CH2Cl2/TFA; MeOH/NH4OH) and purified to give the product. 1H NMR (300 MHz, CD3OD) δ 9.11 (s, 1H), 8.90 (s, 1H), 8.60 (s, 1H), 7.82 (d, 114), 7.28 (d, 1H), 7.18 (s, 1H), 5.52 (m, 1H), 5.10 (d, 2H), 4.90 (d, 2H), 3.74 (s, 2H), 3.53 (m, 1H), 3.12 and 3.04 (2 s, 3H), 2.30 (m, 2H), 2.03 (m, 2H), 1.75 (m, 4H). MS (ES): 595(M+1).

Provenance & Evidence