8-chloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one → Tert-butyl(2,4-dimethyl-1-((6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate

HRID 1398368Notes

Reaction equation

HRID 1398368 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][N:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[N:7]([CH3:16])[C:6]=2[CH:17]=1.[OH:18][CH2:19][C:20]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:25])[CH2:21][CH:22]([CH3:24])[CH3:23]>CCOCC>[C:29]([O:28][C:27](=[O:33])[NH:26][C:20]([CH3:25])([CH2:21][CH:22]([CH3:23])[CH3:24])[CH2:19][O:18][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][N:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[N:7]([CH3:16])[C:6]=2[CH:17]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 867103058-chloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-oneHCID 86710368tert-butyl N-(1-hydroxy-2,4-dimethylpentan-2-yl)carbamate

Product 1

HCID 73213522Tert-butyl(2,4-dimethyl-1-((6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamateYield 111.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8-Chloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (0.15 g, 0.613 mmol), prepared as described in Example 2, Part C, and tert-butyl (1-hydroxy-2,4-dimethylpentan-2-yl)carbamate (0.284 g, 1.226 mmol) were subjected to ether synthesis as described in Example 2, Part D, to afford tert-butyl(2,4-dimethyl-1-((6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate (0.3 g, 28% yield) as pale yellow solid. LC/MS (ESI) m/e 440.2 [(M+H)+, calcd for C25H34N3O4 440.2]; LC/MS retention time (method C): tR=2.67 min.

Sources & evidence

ORD record
ord-93c83a7cc4dc4737ad52428c583c3161
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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