Serinol → 2-(1,3-Dihydroxyprop-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine
Reaction equation
[OH:1][CH2:2][C@H:3]([NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[N:10]2[N:27]=[CH:28][C:29]([CH:30]([CH3:32])[CH3:31])=[C:9]2[N:8]=1)[CH2:4]C.NC(CO)C[OH:36]>>[OH:36][CH2:4][CH:3]([NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:19][CH:20]=2)[N:10]2[N:27]=[CH:28][C:29]([CH:30]([CH3:31])[CH3:32])=[C:9]2[N:8]=1)[CH2:2][OH:1]Participants
3
Procedure
According to the same conditions resulting in the preparation of the compound 2, the compound 17 is prepared from IIa.2 by oxidation reaction of the sulfur atom and then introduction of serinol. Yield=30%. Oil. 1H NMR (300 MHz, CDCl2): δ 8.68 (d, 1H, J=4.4 Hz, Harom), 7.96 (d, 2H, J=8.3 Hz, Harom), 7.79-7.69 (m, 2H, Harom) 7.64 (s, 1H, Harom) 7.45 (d, 2H, J=8.3 Hz, Harom) 7.26-7.21 (m, 1H, Harom), 6.80 (bs, 1H, NH), 5.71 (bs, 1H, NH), 4.77 (d, 2H, J=5.9 Hz, CH2), 4.08-4.95 (m, 1H, CH), 3.92-3.80 (m, 4H, 2 CH2), 3.02 (hept, 1H, J=7.0 Hz, CH), 1.28 (d, 6H, J=7.0 Hz, 2 CH3). MS (ESI): m/z 434 (MH+).