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 1644509Notes

Reaction equation

HRID 1644509 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.[C:36]([O:40][C:41](=[O:64])[NH:42][CH:43]1[CH2:48][CH2:47][N:46]([CH2:49][CH2:50][N:51]2[C:60]3[C:55](=[CH:56][CH:57]=C(OC)C=3)C=C[C:52]2=[O:63])[CH2:45][CH2:44]1)([CH3:39])([CH3:38])[CH3:37]>CO.ClCCl>[C:36]([O:40][C:41](=[O:64])[NH:42][CH:43]1[CH2:44][CH2:45][N:46]([CH2:49][CH2:50][N:51]2[C:52](=[O:63])[CH2:32][O:31][C:29]3[N:28]=[CH:57][C:56]([Br:1])=[CH:55][C:60]2=3)[CH2:47][CH2:48]1)([CH3:39])([CH3:38])[CH3:37]

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-28431ad0302342babce37595bc079d4c
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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