Imidazole → HCID 49869217, compound

HRID 450202Notes

Reaction equation

HRID 450202 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.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1>>[F:27][CH:25]([F:26])[C:15]1[N:14]([C:4]2[N:3]=[C:2]([N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)[N:7]=[C:6]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[N:5]=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 795ImidazoleHCID 534881021-[4-Chloro-6-(morpholin-4-yl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole

Product 1

HCID 49869217HCID 49869217, compoundYield 71%

Procedure

Similarly to Example 63, reaction of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole and imidazole at 120° C. for 1 hr gave 2-(difluoromethyl)-1-[4-(1H-imidazol-1-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-4-methoxy-1H-benzimidazole in 71% yield: mp (CH2Cl2/hexanes) 272-275° C.; 1H NMR (DMSO-d6) δ 8.74 (s, 1H), 8.04 (t, J=1.4 Hz, 1H), 8.00 (d, J=7.8 Hz, 1H), 7.78 (t, JHF=52.5 Hz, 1H), 7.50 (t, J=8.3 Hz, 1H), 7.22 (dd, J=1.5, 0.8 Hz, 1H), 7.02 (d, J=7.8 Hz, 1H), 4.03 (m, 2H), 4.00 (s, 3H), 3.94 (m, 2H), 3.80-3.75 (m, 4H); Anal. Calcd. for C19H18F2N8O2: C, 53.3; H, 4.2: N, 26.2. Found: C, 53.6; H, 4.3; N, 26.7%.

Sources & evidence

ORD record
ord-4e977a1e2a884dbd8aca2babada014f7
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

Loading…