(1S)-2-{[4-carbamoyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]amino}-1-methyl-2-oxoethyl acetate → HCID 136124681, compound
Reaction equation
[OH:1][C@H:2]([C:4]1[NH:5][C:6](=[O:19])[C:7]2[CH:12]=[N:11][N:10]([CH:13]3[CH2:18][CH2:17]OC[CH2:14]3)[C:8]=2[N:9]=1)[CH3:3].C(O[C@@H](C)C(NC1N(C2CCOCC2)N=CC=1C(=O)N)=O)(=O)C>>[CH:13]1([N:10]2[C:8]3[N:9]=[C:4]([C@@H:2]([OH:1])[CH3:3])[NH:5][C:6](=[O:19])[C:7]=3[CH:12]=[N:11]2)[CH2:14][CH2:17][CH2:18]1Participants
3
Procedure
Compound C17 was prepared according to the general procedure for the synthesis of C4 in Example 1, except that C16 was used in place of C3. Additionally, in this case the crude product was purified via silica gel chromatography (Eluant: 50:1 chloroform:MeOH), to afford C17 as a solid. Yield 5.70 g, 24.3 mmol, 87%. LCMS m/z 235.3 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.64 (d, J=6.6 Hz, 3H), 1.91 (m, 2H), 2.44 (m, 2H), 2.75 (m, 2H), 4.26 (br s, 1H), 4.89 (q, J=6.6 Hz, 1H), 5.25 (m, 1H), 8.06 (s, 1H), 11.07 (br s, 1H). 13C NMR (100 MHz, CDCl3) δ 14.93, 22.42, 29.84, 50.92, 67.67, 104.42, 134.66, 151.71, 159.25, 161.48.