Sodium hydride → tert-Butyl{1-[2-(6-bromo-3-oxo-2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-4-yl)ethyl]piperidin-4-yl}carbamate

HRID 1644359Notes

Reaction equation

HRID 1644359 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][C:8](=[O:12])[NH:9][C:10]=2[N:11]=1.[H-].[Na+].CS(O[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][CH2:23]1)(=O)=O.C(OC(=O)NC1CCN(CCN2C3C(=CC=C(OC)C=3)C=CC2=O)CC1)(C)(C)C>>[C:32]([O:31][C:29](=[O:30])[NH:28][CH:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][N:9]2[C:8](=[O:12])[CH2:7][O:6][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[N:11][C:10]2=3)[CH2:23][CH2:24]1)([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 218737726-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-oneHCID 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 86642620tert-Butyl{1-[2-(6-bromo-3-oxo-2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-4-yl)ethyl]piperidin-4-yl}carbamateYield 92%

Procedure

6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (WO 2004/058144) (935 mg, 4.08 mmol) was deprotonated with sodium hydride and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (5.6 mmol) as described for Intermediate 2, but chromatography was omitted, to give the product as a solid in 92% yield.

Sources & evidence

ORD record
ord-b0cd2f596c0d4a05a7eac3e43697032e
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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