3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester → HCID 49785436, compound

HRID 1621768Notes

Reaction equation

HRID 1621768 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:17]2[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:18]=2)[C:5]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1.[O:43]1[CH2:48][CH:47]=[C:46](B2OC(C)(C)C(C)(C)O2)[CH2:45][CH2:44]1>>[O:43]1[CH2:44][CH:45]=[C:46]([C:2]2[CH:3]=[C:4]([C:17]3[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=3)[C:5]([NH:8][C:9]3[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)=[N:6][CH:7]=2)[CH2:47][CH2:48]1

Participants

3

Reactant 2

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 666119674-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 49785436HCID 49785436, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 247 using 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Frontier Scientific), and was isolated as a yellow amorphous solid (35%). m/z (ESI, +ve ion) 392.0 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.76 (1H, s); 8.83 (1H, d, J=2.5 Hz); 8.54 (1H, d, J=2.7 Hz); 8.44 (1H, d, J=2.5 Hz); 8.17 (1H, dd, J=8.8, 2.7 Hz); 7.87 (1H, br. s.); 7.73 (1H, br. s.); 6.83 (1H, d, J=8.8 Hz); 6.22 (1H, br. s.); 4.24 (2H, d, J=2.5 Hz); 3.82-3.87 (5H, m); 2.47 (2H, m); 2.44 (3H, s).

Sources & evidence

ORD record
ord-0022111e2919457e85c17470059a37cc
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…