2-[(1-Adamantylmethyl)amino]nicotinic acid → 1-(1-adamantylmethyl)-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione

HRID 601110Notes

Reaction equation

HRID 601110 reaction equation
[C:1]12([CH2:11][NH:12][C:13]3[N:21]=[CH:20][CH:19]=[CH:18][C:14]=3[C:15]([OH:17])=[O:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(C(CC)CNC1N=CC=CC=1[C:29](OCC)=[O:30])C>>[C:1]12([CH2:11][N:12]3[C:13]4[N:21]=[CH:20][CH:19]=[CH:18][C:14]=4[C:15](=[O:17])[O:16][C:29]3=[O:30])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

3

Reactant 2

HCID 670640232-[(1-Adamantylmethyl)amino]nicotinic acidHCID 67064133Ethyl 2-[(2-ethylbutyl)amino]nicotinate

Product 1

HCID 865921041-(1-adamantylmethyl)-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 34A for the product of Example 3A (0.025 g, 20%). 1H NMR (300 MHz, CDCl3) δ 1.74 (m, 12H), 2.04 (s, 3H), 3.65 (d, J=5.88 Hz, 2H), 6.91 (dd, J=7.72, 5.52 Hz, 1H), 8.51 (d, J=4.78 Hz, 1H), 8.77 (d, J=7.72 Hz, 1H).

Sources & evidence

ORD record
ord-c0316c2ad2ed41bf9fd2de8e0cda90c4
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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