Sodium hydride → 5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(8-methyl-8-azabicyclo [3.2.1]oct-3-yl)oxy]-1,6-naphthyridin-2(1H)-one

HRID 394154Notes

Reaction equation

HRID 394154 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:20])[N:9]2[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[N:3]=1.[CH3:28][N:29]1[C@@H:33]2[CH2:34][C@H:35]([OH:37])[CH2:36][C@H:30]1[CH2:31][CH2:32]2.BrC1C=C(CO)C=C2C=1CN(CC1C=CC(OC)=CC=1)C(=O)N2C1C(Cl)=CC=CC=1Cl.[H-].[Na+]>>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:4]1[N:3]=[C:2]([O:37][CH:35]2[CH2:34][CH:33]3[N:29]([CH3:28])[CH:30]([CH2:31][CH2:32]3)[CH2:36]2)[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:20])[N:9]2[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:19]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 226479525-bromo-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-oneHCID 22647982HCID 22647982, compoundHCID 178481185HCID 178481185, compound

Product 1

HCID 226481265-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(8-methyl-8-azabicyclo [3.2.1]oct-3-yl)oxy]-1,6-naphthyridin-2(1H)-one

Procedure

The title compound was prepared from 100 mg of 7-bromo-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (COMPOUND HHH2), 147 mg of a ca. 1.4:1 mixture of pseudotropine and tropine (EXAMPLE HHH9, Step A), and 25 mg of NaH by a procedure analogous to that described in COMPOUND HHH6.

Sources & evidence

ORD record
ord-9fa6abd9efbb43fb9ee083909513095b
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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