Diisopropylethylamine → HCID 58369003, compound

Participants

Reaction Conditions

Reaction Steps

2-Methyl-3-(triisopropylsilyloxy)propanoic acid (34 mg, 0.12 mmol), HATU (50 mg, 0.12 mmol), and DIPEA (0.023 mL, 0.12 mmol) were stirred in dry DMF (3 mL) for 1 h before 17 (40 mg, 0.118 mmol) was added at rt. The stirring was continued for 1 h before it was heated at 100° C. for 5 h. After cooling, TBAF (1 ml, 1 M in THF) was added and stirred for 5 h at rt. After filtration, the mixture was purified by preparative LC/MS to give 3-(5-(5-(1-hydroxypropan-2-yl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (A67) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 9.06 (s, 1H), 8.03 (s, 1H), 7.91 (s, 1H), 7.42 (d, J=2.4 Hz, 1H), 7.35 (dd, J=2.4, 8.0 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 3.82 (m, 2H), 3.35 (s, 3H), 3.18 (m, 1H), 2.86 (s, 3H), 2.16 (s, 3H), 1.35 (d, J=7.2 Hz, 3H). MS m/z 406.2 (M+1).

Provenance & Evidence