3-Pyridinylboronic acid → HCID 49869080, compound

HRID 450184Notes

Reaction equation

HRID 450184 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:17]=3[N:16]=[C:15]2[CH:25]([F:27])[F:26])[N:3]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1>>[F:26][CH:25]([F:27])[C:15]1[N:14]([C:4]2[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:7]=[C:2]([C:30]3[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=3)[N:3]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:17]=2[N:16]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 534881021-[4-Chloro-6-(morpholin-4-yl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole

Product 1

HCID 49869080HCID 49869080, compoundYield 61%

Procedure

Reaction of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole (Example 2) and 3-pyridinylboronic acid, as in Example 47, gave 2-(difluoromethyl)-4-methoxy-1-[4-(4-morpholinyl)-6-(3-pyridinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole in 61% yield: mp (CH2Cl2/MeOH) 208-210° C.; 1H NMR (DMSO-d6) δ 9.59 (dd, J=2.2, 0.7 Hz, 1H), 8.85 (dd, J=4.8, 1.7 Hz, 1H), 8.75 (dt, J=8.0, 1.9 Hz, 1H), 8.35 (dd, J=8.4, 0.4 Hz, 1H), 7.83 (t, Jjw=52.6 Hz, 1H), 7.66 (ddd, J=8.0, 4.8, 0.8 Hz, 1H), 7.50 (t, J=8.3 Hz, 1H), 7.02 (d, J=7.8 Hz, 1H), 4.09 (t, J=7.8 Hz, 2H), 4.00 (s, 3H), 3.94 (m, 2H), 3.78 (m, 4H); Anal. Calcd. for C21H19F2N7O40.3H2O: C, 56.7; H, 4.4; N, 22.0. Found: C, 56.6; H, 4.0; N, 22.1%.

Sources & evidence

ORD record
ord-f65a928e95944855bb5a3b8e5045d487
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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