tert-butyl N-(1-hydroxy-2,4-dimethylpentan-2-yl)carbamate → Tert-butyl(1-((9-methoxy-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-2,4-dimethylpentan-2-yl)carbamate

HRID 1398386Notes

Reaction equation

HRID 1398386 reaction equation
Cl[C:2]1[C:3]([O:19][CH3:20])=[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:21][CH2:22][C:23]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:28])[CH2:24][CH:25]([CH3:27])[CH3:26]>>[C:32]([O:31][C:30](=[O:36])[NH:29][C:23]([CH3:28])([CH2:24][CH:25]([CH3:26])[CH3:27])[CH2:22][O:21][C:2]1[C:3]([O:19][CH3:20])=[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)([CH3:35])([CH3:34])[CH3:33]

Participants

3

Reactant 2

HCID 86710368tert-butyl N-(1-hydroxy-2,4-dimethylpentan-2-yl)carbamateHCID 867103738-chloro-9-methoxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one

Product 1

HCID 89957263Tert-butyl(1-((9-methoxy-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-2,4-dimethylpentan-2-yl)carbamateYield 21%

Procedure

8-Chloro-9-methoxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (0.04 g, 0.139 mmol) was subjected to Buchwald coupling (Example 16, Part H) with tert-butyl (1-hydroxy-2,4-dimethylpentan-2-yl)carbamate (0.048 g, 0.208 mmol) which afforded tert-butyl(1-((9-methoxy-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-2,4-dimethylpentan-2-yl)carbamate as white solid (15 mg, 0.029 mmol, 21% yield). LC/MS (ESI) m/e 484.2 [(M+H)+, calcd for C22H38N3O5, 484.3]; LC/MS retention time (Method C): tR=2.42 min.

Sources & evidence

ORD record
ord-ce46e4e995694277b855e65a27b24e1f
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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