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

HRID 255375Notes

Reaction equation

HRID 255375 reaction equation
[Br:1][C:2]1[CH:28]=[N:27][C:5]2[O:6][CH2:7][C:8](=[O:26])[N:9]([CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14][CH2:13]3)[C:4]=2[CH:3]=1.NC1CCN(CCN2C3C(=CC=C(C#N)C=3)C=CC2=O)CC1>>[NH2:18][CH:15]1[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][N:9]2[C:8](=[O:26])[CH2:7][O:6][C:5]3[N:27]=[CH:28][C:2]([Br:1])=[CH:3][C:4]2=3)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 602009201-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrileHCID 86642663tert-Butyl{1-[2-(7-bromo-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethyl]piperidin-4-yl}carbamate2×

Product 1

HCID 667742821-[2-(4-Aminopiperidin-1-yl)ethyl]-7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

Procedure

tert-Butyl {1-[2-(7-bromo-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 210) (0.85 g) 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-40d7498453dd472f97ab0bb56eb83bc4
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

Loading…