Sodium Methoxide → [4-(Dimethylamino)-2-(1-methylethoxy)-3-phenylquinolin-6-yl](1-methyl-1H-imidazol-5-yl)pyridin-4-ylmethanol.TFA

HRID 627552Notes

Reaction equation

HRID 627552 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([N:18]([CH3:20])[CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:21]([C:29]3[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[OH:22])[CH:8]=2)[N:3]=1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36].[O:42]([CH:44]([CH3:46])[CH3:45])[Na].C[O-].[Na+]>CC(O)C.CO>[CH3:19][N:18]([CH3:20])[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:21]([C:29]3[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[OH:22])[CH:8]=2)[N:3]=[C:2]([O:42][CH:44]([CH3:46])[CH3:45])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 86716112(2-Chloro-4-(dimethylamino)-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)pyridin-4-ylmethanol.TFAHCID 178459997HCID 178459997, compound

Product 1

HCID 86716111[4-(Dimethylamino)-2-(1-methylethoxy)-3-phenylquinolin-6-yl](1-methyl-1H-imidazol-5-yl)pyridin-4-ylmethanol.TFA

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

The title compound was prepared using (2-chloro-4-(dimethylamino)-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(pyridin-4-yl)methanol (Example 47) and NaOiPr in iPrOH in place of (3-chlorophenyl)(2,4-dichloro-3-phenylquinolin-6-yl)(pyridin-3-yl)methanol and NaOMe in MeOH, respectively, according to the procedure described in Example 79. 1H NMR (400 MHz, MeOH-d4) δ 9.08 (s, 1H), 8.84 (d, J=6.11 Hz, 2H), 8.11 (s, 1H), 8.05 (d, J=6.11 Hz, 2H), 7.87 (d, J=8.80 Hz, 1H), 7.64 (d, J=8.80 Hz, 1H), 7.33-7.50 (m, 3H), 7.16-7.27 (m, 3H), 5.32-5.50 (m, 1H), 3.72 (s, 3H), 2.59 (s, 6H), 1.23 (d, J=6.11 Hz, 6H); MS m/e 494.2 [M+H]+.

Sources & evidence

ORD record
ord-b754fdb3e7be4a8692ccf225da027e10
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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