Methyl iodide → Diethyl 2-((Methyl(2-(morpholin-4-ylmethyl)-1,3-thiazol-5-yl)amino)methylene)-malonate

HRID 1070627Notes

Reaction equation

[N:1]1([CH2:7][C:8]2[S:9][C:10]([NH:13][CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:26]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:26][N:13]([CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]1[S:9][C:8]([CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[N:12][CH:11]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a mixture of diethyl 2-(((2-(morpholin-4-ylmethyl)-1,3-thiazol-5-yl)amino)-methylene)malonate (Preparation 28, 1.51 g) and K2CO3 (1.19 g) in DMF (15 mL) at ambient temperature is added iodomethane (0.28 mL). The mixture is heated to 75° C. in a sealed pressure tube and stirred overnight. The solution is cooled to ambient temperature and the solvent is removed. The mixture is diluted with water (75 mL) and extracted with EtOAc (3×75 mL). The organic layer is dried (MgSO4) and the solvent removed to afford 0.984 g (63%) of the title compound as a light brown solid. Physical characteristics: 1H NMR (CDCl3) δ1.24-1.33, 2.60, 3.31, 3.74, 4.17-4.24, 7.60; IR (liq.) 1702, 1608, 1535, 1453, 1383, 1365, 1293, 1270, 1232, 1206, 1117, 1096, 1071, 1010, 865 cm−1; HRMS (FAB) m/z 384.1600 (C17H25N3O5S+H). Anal. Found: C, 53.18; H, 6.64; N, 10.41.

Workup

temperatureThe solution is cooled to ambient temperature
customthe solvent is removed
additionThe mixture is diluted with water (75 mL)
extractionextracted with EtOAc (3×75 mL)
dry with materialThe organic layer is dried (MgSO4)
customthe solvent removed

Sources & evidence

ORD record: ord-4762592d4a944f2f82f5af6a94b7e014
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903097B2

Reaction notes

Loading…