Sodium hydride → tert-Butyl {1-[2-(7-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 255181Notes

Reaction equation

HRID 255181 reaction equation
FC1C=C2C(C=CC(=O)N2)=CC=1.[H-].[Na+].CS(OCCN1CCC(NC(OC(C)(C)C)=O)CC1)(=O)=O.[F:36][C:37]1[C:46](F)=[C:45]2[C:40]([CH:41]=[CH:42][C:43](=[O:64])[N:44]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:39][CH:38]=1>>[F:36][C:37]1[CH:46]=[C:45]2[C:40]([CH:41]=[CH:42][C:43](=[O:64])[N:44]2[CH2:48][CH2:49][N:50]2[CH2:51][CH2:52][CH:53]([NH:56][C:57](=[O:63])[O:58][C:59]([CH3:60])([CH3:61])[CH3:62])[CH2:54][CH2:55]2)=[CH:39][CH:38]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 190675757-Fluoroquinolin-2(1H)-one2×HCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate2×HCID 86642603tert-butyl{1-[2-(7,8-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 86635312tert-Butyl {1-[2-(7-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Procedure

7-Fluoroquinolin-2(1H)-one (Intermediate 29) (500 mg, 3.06 mmol) was deprotonated with sodium hydride (135 mg, 60% in oil, 3.37 mmol) and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (3.7 mmol) as described for Intermediate 20. Colorless solid, 570 mg (48%).

Sources & evidence

ORD record
ord-b233f089cf50474aa66137bf64cab20d
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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