8-Chloro-4,6-dimethyl-5H,6H-benzo[c]2,7-naphthyridin-5-one → Tert-butyl(1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-2,4-dimethylpentan-2-yl)carbamate

HRID 1398380Notes

Reaction equation

HRID 1398380 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1.[OH:19][CH2:20][C:21]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:26])[CH2:22][CH:23]([CH3:25])[CH3:24]>>[C:30]([O:29][C:28](=[O:34])[NH:27][C:21]([CH3:26])([CH2:22][CH:23]([CH3:24])[CH3:25])[CH2:20][O:19][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

3

Reactant 2

HCID 867103378-Chloro-4,6-dimethyl-5H,6H-benzo[c]2,7-naphthyridin-5-oneHCID 86710368tert-butyl N-(1-hydroxy-2,4-dimethylpentan-2-yl)carbamate

Product 1

HCID 89957266Tert-butyl(1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-2,4-dimethylpentan-2-yl)carbamateYield 34.3%

Procedure

8-Chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (0.15 g, 0.580 mmol), prepared as described in Example 16, Part G, and tert-butyl (1-hydroxy-2,4-dimethylpentan-2-yl)carbamate (0.161 g, 0.696 mmol) were subjected to the Buchwald coupling as described in Example 16, Part H, to afford tert-butyl(1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-2,4-dimethylpentan-2-yl)carbamate (0.22 g, 0.199 mmol, 34% crude yield). Crude product was used for next step without further purification. LC/MS (ESI) m/e 454.1 [(M+H)+, calcd for C26H36N3O4, 454.3]; LC/MS retention time (method D): tR=0.93 min.

Sources & evidence

ORD record
ord-47bc89f070f6495fa5e0755b1581cda6
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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