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 1644361Notes

Reaction equation

HRID 1644361 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:20]=3[O:19][CH2:18][C:17]2=[O:29])[CH2:10][CH2:9]1)(C)(C)C.NC1CCN(CCN2C3C(=CC=C(C#N)C=3)C=CC2=O)CC1>>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:20]=3[O:19][CH2:18][C:17]2=[O:29])[CH2:10][CH2:9]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-1ee3660f90c74115935557590cbae582
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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