(5-Fluoropyridin-3-yl)boronic acid → HCID 49785439, compound

HRID 1621761Notes

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.[F:43][C:44]1[CH:45]=[C:46](B(O)O)[CH:47]=[N:48][CH:49]=1>>[NH2:24][C:19]1[N:20]=[C:21]([CH3:23])[N:22]=[C:17]([C:4]2[CH:3]=[C:2]([C:46]3[CH:47]=[N:48][CH:49]=[C:44]([F:43])[CH:45]=3)[CH:7]=[N:6][C:5]=2[NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[N:18]=1

Participants

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acid

HCID 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 49785439HCID 49785439, 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 5-fluoropyridin-3-ylboronic acid (Combi-Blocks Inc.), and was isolated as an orange crystalline solid (22%). m/z (ESI, +ve ion) 405.0 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.90 (1H, s); 9.09 (1H, d, J=2.7 Hz); 8.80 (1H, s); 8.75 (1H, d, J=2.7 Hz); 8.56 (2H, t, J=2.5 Hz); 8.19 (1H, dd, J=8.9, 2.8 Hz); 8.10 (1H, br s.); 7.92 (1H, br. s.); 7.77 (1H, br. s.); 6.86 (1H, d, J=9.0 Hz); 3.86 (3H, s), 2.47 (3H, s).

Sources & evidence

ORD record: ord-d711333101174dc19064a74fe4c9b4aa
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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