ethyl 2-{[(1R)-1-phenylethyl]amino}nicotinate → 1-[(1R)-1-phenylethyl]-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione

HRID 601113Notes

Reaction equation

HRID 601113 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]2[N:20]=[CH:19][CH:18]=[CH:17][C:11]=2[C:12]([O:14][CH2:15]C)=[O:13])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C(CC)CNC1N=CC=CC=1C(OCC)=[O:29])C>>[C:1]1([C@H:7]([N:9]2[C:10]3[N:20]=[CH:19][CH:18]=[CH:17][C:11]=3[C:12](=[O:13])[O:14][C:15]2=[O:29])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 29031481ethyl 2-{[(1R)-1-phenylethyl]amino}nicotinateHCID 67064133Ethyl 2-[(2-ethylbutyl)amino]nicotinate

Product 1

HCID 865921071-[(1R)-1-phenylethyl]-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione

Procedure

The title compound was prepared according to the procedure of Example 3B substituting the product of Example 57A for the product of Example 3A (0.250 g, 62%). 1H NMR (300 MHz, DMSO-d6) δ 1.86 (d, J=6.99 Hz, 3H), 6.65 (q, J=6.99 Hz, 1H), 7.27 (m, 3H), 7.40 (m, 3H), 8.43 (dd, J=7.72, 1.84 Hz, 1H), 8.73 (dd, J=4.96, 2.02 Hz, 1H).

Sources & evidence

ORD record
ord-89c2e69d9295472f8e82be20081e1f70
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

Loading…