Urea → HCID 10203994, compound

HRID 1760371Notes

Reaction equation

HRID 1760371 reaction equation
[N:1]1[C:2](=[O:9])[NH:3]C(=O)C(=O)C=1.C(O[C:13]([C:15]1([C:40]([O:42]CC)=O)[CH2:19][CH2:18][C:17](=[O:20])[N:16]1[C:21]1[CH:22]=[N:23][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][N:35]3[CH:39]=[CH:38][CH:37]=[N:36]3)=[CH:30][CH:29]=2)=[CH:25][CH:26]=1)=[O:14])C.NC(N)=O>[O-]CC.[Na+].C(O)C>[N:35]1([CH2:34][C:31]2[CH:30]=[CH:29][C:28]([O:27][C:24]3[N:23]=[CH:22][C:21]([N:16]4[C:15]5([C:13](=[O:14])[NH:3][C:2](=[O:9])[NH:1][C:40]5=[O:42])[CH2:19][CH2:18][C:17]4=[O:20])=[CH:26][CH:25]=3)=[CH:33][CH:32]=2)[CH:39]=[CH:38][CH:37]=[N:36]1

Participants

6

Reactant 3

HCID 1176UreaHCID 20558234HCID 20558234, compoundHCID 69743545HCID 69743545, compound

Product 1

HCID 10203994HCID 10203994, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

Following the procedure for pyrimidinetrione formation outlined in Example 1, reaction of 5-oxo-1-[6-(4-pyrazol-1-ylmethyl-phenoxy)-pyridin-3-yl]-pyrrolidine-2,2-dicarboxylic acid diethyl ester (0.2 g, 0.4 mmol) with urea (0.074 g, 1.2 mmol) in 1.2 mL of 1M sodium ethoxide in ethanol afforded 6 mg of 1-[6-(4-Pyrazol-1-ylmethyl-phenoxy)-pyridin-3-yl]-1,7,9-triaza-spiro[4.5]decane-2,6,8,10-tetraone as a colorless solid. 1H NMR (CD3OD, 500 MHz): 7.99 (d, 1H, J=2.5 Hz), 7.72 (m, 2H), 7.53 (d, 1H, J=2.5 Hz), 7.29 (d, 2H, J=8.5 Hz 7.10 (d, 2H, J=8.5 Hz), 6.97 (d, 1H, J=8.5 Hz), 6.35 (t, 1H, J=2.0 Hz), 5.38 (s, 2H), 2.75 (m, 2H), 2.65 (m, 2H) ppm. MS (APCl, m/z): 447.2 [M+H]+.

Sources & evidence

ORD record
ord-0aca962d2944408fb2ac57c473473b64
Source dataset
uspto-grants-2005_01
Patent number
US06841671B2

Reaction notes

Loading…