2-Methoxyethylamine → N-(2-methoxyethyl)-N'-[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]urea

HRID 1715276Notes

Reaction equation

HRID 1715276 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:20][C:21]([N:23]2[CH:27]=[CH:26]N=C2)=[O:22])[S:5][C:6]=1[C:7]1[N:8]=[C:9]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[S:10][CH:11]=1.[CH3:28][O:29]CCN>CN(C=O)C>[CH3:28][O:29][CH2:26][CH2:27][NH:23][C:21]([NH:20][C:4]1[S:5][C:6]([C:7]2[N:8]=[C:9]([C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[O:13])[S:10][CH:11]=2)=[C:2]([CH3:1])[N:3]=1)=[O:22]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 59465567N-[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]-1H-imidazole-1-carboxamide

Product 1

HCID 11989985N-(2-methoxyethyl)-N'-[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-[4′-methyl-2-(morpholin-4-ylcarbonyl)-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide, prepared in Step III, described above (50 mg; 0.17 mmol; 1 eq.), is added DMF (2 ml) and 2-methoxyethylamine (Fluka)(16 μl; 0.19 mmol; 1.10 eq.). The mixture is stirred 10 min at rt. Solvents are evaporated and the crude product is crystallized in MeOH, affording Compound (36) as a white-off solid (42.1 mg; 60%). 1H NMR (DMSO-d6, 300 MHz) δ 2.41 (s, 3H), 3.30 (m, 5H), 3.39 (m, 2H), 3.68 (m, 6H), 4.33 (m, 2H), 6.67 (m, 1H), 7.91 (s, 1H), 10.41 (br s, 1H). M− (ESI): 410.09; M+ (ESI): 412.12. HPLC (method A), Rt: 2.41 min (purity: 99.7%).

Workup

  1. customSolvents are evaporated
  2. customthe crude product is crystallized in MeOH

Sources & evidence

ORD record
ord-dfe976476ce64b33b214e6ff945c28dd
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

Loading…