1-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile → 4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 255241Notes

Reaction equation

HRID 255241 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[N:9]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([NH:22]C(=O)OC(C)(C)C)[CH2:18][CH2:17]3)[C:8]=2[CH:30]=1)([O-:3])=[O:2].NC1CCN(CCN2C3C(=CC=C(C#N)C=3)C=CC2=O)CC1>>[NH2:22][CH:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][N:9]2[C:8]3[CH:30]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=3[O:12][CH2:11][C:10]2=[O:13])[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 602009201-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrileHCID 86642621tert-Butyl{1-[2-(6-nitro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}carbamate2×

Product 1

HCID 667749044-[2-(4-Aminopiperidin-1-yl)ethyl]-6-nitro-2H-1,4-benzoxazin-3(4H)-one

Procedure

tert-Butyl {1-[2-(6-nitro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 82) was reacted as described for Intermediate 14. The crude trifluoro acetate of the title compound was used without further purification for the next step (quantitative yield).

Workup

  1. customThe crude trifluoro acetate of the title compound was used without further purification for the next step (quantitative yield)

Sources & evidence

ORD record
ord-afd504e798af45bebf5fd9b9cb6b3880
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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