Diisopropylethylamine → HCID 56951875, compound

Participants

Reaction Conditions

Reaction Steps

To a solution containing AWS-I-45 (16 mg, 0.047 mmol) in 1 mL DMF was added 1H-pyrazole-1-carboxamidine hydrochloride (13.9 mg, 0.095 mmol), N,N-diisopropylethylamine, (41 μL, 0.237 mmol) and a stir bar. The solution was heated to 100° C. for 16 hours and then allowed to cool. The light-red reaction mixture was diluted with 1.5 mL of MeCN/H2O (1:1) and purified by HPLC to give 9 mg (48%) of AWS-I-169 as a clear amorphous solid; [α]D25=−3.2° (c=0.72, MeOH) 1H NMR (500 MHz, CD3OD): δ 8.3 (br s, 1Hformate), 7.84 (dd J=2.5, 11.5 Hz, 1H), 7.50 (d, J=8.75 Hz, 1H), 7.43 (t, J=8.5 Hz, 1H)), 7.34-7.29 (m, 4H), 5.27 (d, J=4.5 Hz, 1H), 4.30 (m, 1H), 3.52 (dd, J=7.5 Hz, 1H), 2.93 (dd, J=5, 16.5 Hz, 1H); 13C NMR (125 MHz, CD3OD) δ 162.8, 159.4, 159.3, (d, JCF=244.4 Hz), 159.0, 141.9, 139.7, 139.1 (d, JCF=9.8 Hz), 131.9, 130.6, 129.0, 126.4, 126.3, 118.3 (d, JCF=3.3 Hz), 117.4 (d, JCF=17.8 Hz), 110.0 (d, JCF=26.3 Hz), 62.3, 59.7, 37.8. HRMS (ES+) m/z 390.1132 [(M+H)+; calcd for C18H18ClFN5O2: 390.1133].

Provenance & Evidence