(6-Methoxypyridin-3-yl)(1-methyl-1H-imidazol-5-yl)methanone → (4-Chloro-2-(dimethylamino)-3-phenoxyquinolin-6-yl)(6-methoxypyridin-3-yl)(1-methyl-1H-imidazol-5-yl)methanol

HRID 623979Notes

Reaction equation

HRID 623979 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([CH2:15]C)[CH2:13]C)[C:6]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[C:5]2[Cl:24].[CH3:25][O:26][C:27]1[N:32]=[CH:31][C:30]([C:33]([C:35]2[N:39]([CH3:40])[CH:38]=[N:37][CH:36]=2)=[O:34])=[CH:29][CH:28]=1>>[Cl:24][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:33]([C:30]3[CH:31]=[N:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)([C:35]3[N:39]([CH3:40])[CH:38]=[N:37][CH:36]=3)[OH:34])[CH:3]=2)[N:8]=[C:7]([N:12]([CH3:15])[CH3:13])[C:6]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 86715443(6-Methoxypyridin-3-yl)(1-methyl-1H-imidazol-5-yl)methanone2×HCID 867154626-bromo-4-chloro-N,N-diethyl-3-phenoxyquinolin-2-amine2×

Product 1

HCID 74223842(4-Chloro-2-(dimethylamino)-3-phenoxyquinolin-6-yl)(6-methoxypyridin-3-yl)(1-methyl-1H-imidazol-5-yl)methanol

Procedure

The title compound was prepared using 6-bromo-4-chloro-N,N-dimethyl-3-phenoxyquinolin-2-amine (Intermediate 5, step e) and (6-methoxypyridin-3-yl)(1-methyl-1H-imidazol-5-yl)methanone (Intermediate 4, step d) according to the procedure of Example 3a. 1H NMR (400 MHz, MeOH-d4) δ 8.01 (d, J=2.02 Hz, 1H), 7.93 (d, J=2.02 Hz, 1H), 7.72-7.86 (m, 2H), 7.68 (dd, J=2.53, 8.59 Hz, 1H), 7.56 (dd, J=2.02, 9.09 Hz, 1H), 7.25-7.32 (m, J=7.07, 8.59 Hz, 2H), 7.01-7.07 (m, 1H), 6.81 (d, J=8.59 Hz, 1H), 6.72-6.78 (m, 2H), 6.37 (br. s., 1H), 3.91 (s, 3H), 3.51 (s, 3H), 3.11 (s, 6H); MS m/e 516.9 [M+H]+.

Sources & evidence

ORD record
ord-b34bb973ebee42c5a4d1332f45a0a88e
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Reaction notes

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