Sodium hydride → HCID 178487287, compound

HRID 1644353Notes

Reaction equation

HRID 1644353 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=2[CH:13]=1.[H-].[Na+].CS(O[CH2:21][CH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][CH2:24]1)(=O)=O.C(OC(=O)NC1CCN(CCN2C3C(=CC=C(OC)C=3)C=CC2=O)CC1)(C)(C)C>ClCCl.CO>[C:33]([O:32][C:30](=[O:31])[NH:29][C@H:26]1[CH2:25][CH2:24][C@H:23]([CH2:22][CH2:21][N:8]2[C:7]3[CH:13]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[O:11][CH2:10][C:9]2=[O:12])[CH2:28][CH2:27]1)([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 132049526-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one2×HCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamateHCID 178453928HCID 178453928, compound2×

Product 1

HCID 178487287HCID 178487287, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

6-Methoxy-2H-1,4-benzoxazin-3(4H)-one (Intermediate 48) (310 mg, 1.73 mmol) was deprotonated with sodium hydride and alkylated with 2-{trans-4-[(tert butoxycarbonyl)amino]cyclohexyl}ethyl methanesulfonate (Intermediate 76) (2 mmol) as described for Intermediate 2. Chromatography on silica gel with dichloromethane/methanol (20:1) afforded the product as a solid (58%).

Sources & evidence

ORD record
ord-dfac912340c04c209ce8c8957667d72b
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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