1-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile → 4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1644358Notes

Reaction equation

HRID 1644358 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](=[O:22])[CH2:20][O:19][C:18]3[CH:23]=[CH:24][C:25]([Br:27])=[N:26][C:17]2=3)[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](=[O:22])[CH2:20][O:19][C:18]3[CH:23]=[CH:24][C:25]([Br:27])=[N:26][C:17]2=3)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 602009201-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrileHCID 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}carbamate2×

Product 1

HCID 866426194-[2-(4-Aminopiperidin-1-yl)ethyl]-6-bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Procedure

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 (Intermediate 80) 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-848b46001644418898e43c2726f950cc
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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