Sodium hydride → tert-Butyl{1-[2-(7-bromo-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethyl]piperidin-4-yl}carbamate

HRID 255376Notes

Reaction equation

HRID 255376 reaction equation
[Br:1]C1C=CC2OCC(=O)NC=2N=1.[H-].[Na+].CS(OCCN1CCC([NH:28][C:29]([O:31][C:32](C)(C)C)=O)CC1)(=O)=O.COC1C=[C:46]2[C:41](C=C[C:44](=[O:64])[N:45]2[CH2:48][CH2:49][N:50]2[CH2:55][CH2:54][CH:53]([NH:56][C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])[CH2:52][CH2:51]2)=[CH:40][CH:39]=1>CO.ClCCl>[Br:1][C:40]1[CH:39]=[N:28][C:29]2[O:31][CH2:32][C:44](=[O:64])[N:45]([CH2:48][CH2:49][N:50]3[CH2:55][CH2:54][CH:53]([NH:56][C:57](=[O:63])[O:58][C:59]([CH3:60])([CH3:61])[CH3:62])[CH2:52][CH2:51]3)[C:46]=2[CH:41]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 218737726-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one2×HCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate2×HCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 86642663tert-Butyl{1-[2-(7-bromo-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethyl]piperidin-4-yl}carbamateYield 93%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (Intermediate 211) (460 mg, 2.0 mmol) was deprotonated with sodium hydride and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (2.1 mmol) as described for Intermediate 2. Chromatography on silica gel with methanol/dichloromethane gave the product as an oil (0.85 g, 93% yield).

Sources & evidence

ORD record
ord-1dab58616c664e7fa334fc15a52fc29b
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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