ethyl 2-({[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)nicotinate → 1-{[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl]-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione

HRID 601108Notes

Reaction equation

HRID 601108 reaction equation
[CH3:1][C:2]1([CH3:22])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][NH:10][C:11]1[N:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16]C)=[O:14].C(C(CC)CNC1N=CC=CC=1C(OCC)=[O:31])C>>[CH3:22][C:2]1([CH3:1])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][N:10]1[C:11]2[N:21]=[CH:20][CH:19]=[CH:18][C:12]=2[C:13](=[O:14])[O:15][C:16]1=[O:31]

Participants

3

Reactant 2

HCID 67063535ethyl 2-({[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)nicotinateHCID 67064133Ethyl 2-[(2-ethylbutyl)amino]nicotinate

Product 1

HCID 865923121-{[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl]-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 31A for the product of Example 3A (0.570 g, 95%). 1H NMR (300 MHz, DMSO-d6) δ 0.79 (d, J=9.56 Hz, 1H), 1.14 (s, 3H), 1.22 (s, 3H), 1.62 (m, 1H), 1.87 (m, 5H), 2.26 (m, 1H), 2.53 (m, 1H), 4.04 (dd, J=13.05, 6.07 Hz, 1H), 4.28 (dd, J=13.24, 9.19 Hz, 1H), 7.37 (dd, J=7.72, 4.78 Hz, 1H), 8.38 (dd, J=7.72, 1.84 Hz, 1H), 8.76 (dd, J=4.78, 1.84 Hz, 1H).

Sources & evidence

ORD record
ord-a02b315252d94d17ab92cd8890789afd
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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