1-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile → 4-[2-(6-Amino-3-azabicyclo[3.1.0]hex-3-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

HRID 255253Notes

Reaction equation

HRID 255253 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:15]3[CH2:20][CH:19]4[CH:17]([CH:18]4[NH:21]C(=O)OC(C)(C)C)[CH2:16]3)[C:7]=2[CH:29]=1)#[N:2].NC1CCN(CCN2C3C(=CC=C(C#N)C=3)C=CC2=O)CC1>>[NH2:21][CH:18]1[CH:19]2[CH:17]1[CH2:16][N:15]([CH2:14][CH2:13][N:8]1[C:7]3[CH:29]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[O:11][CH2:10][C:9]1=[O:12])[CH2:20]2

Participants

3

Reactant 2

HCID 602009201-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrileHCID 86642625tert-Butyl {3-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-3-azabicyclo[3.1.0]hex-6-yl}carbamate2×

Product 1

HCID 667753604-[2-(6-Amino-3-azabicyclo[3.1.0]hex-3-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

Procedure

tert-Butyl {3-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-3-azabicyclo[3.1.0]hex-6-yl}carbamate (Intermediate 94) was reacted as described for Intermediate 14. The crude trifluoro acetate of the title compound was obtained as a colorless solid and used without further purification for the next step (quantitative yield).

Sources & evidence

ORD record
ord-ea4d25ad9a0e4983b92d11d2ca0cb2cc
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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