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

HRID 1715280Notes

Reaction equation

HRID 1715280 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:20][C:21]([N:23]2C=CN=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.N.O1CCOCC1>CN(C=O)C>[CH3:1][C:2]1[N:3]=[C:4]([NH:20][C:21]([NH2:23])=[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

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 312751,4-Dioxane2×HCID 59465567N-[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]-1H-imidazole-1-carboxamide

Product 1

HCID 11989989N-[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 as in Step III of Example 36, described above (535 mg; 1.33 mmol) is added DMF (20 ml) and ammonia 0.5 M solution in dioxane (3.20 ml; 0.50 M; 1.60 mmol; 1.10 eq.). The mixture is stirred at rt overnight. Some ammonia 0.5 M solution in dioxane (1.46 ml; 0.50 M; 0.73 mmol; 0.50 eq.) is added and the mixture is stirred at rt for 5 additional hours. As the reaction is complete, solvents are evaporated. The resulting crude yellow product is purified by preparative HPLC, affording Compound (40) as white-off powder (177 mg; 26%). 1H NMR (DMSO-d6, 300 MHz) δ 2.41 (s, 3H), 3.68 (m, 6H), 4.32 (m, 2H), 6.42 (br s, 2H), 7.91 (s, 1H), 10.45 (br s, 1H). M− (ESI): 352.12; M+ (ESI): 354.11. HPLC (method A), Rt: 2.03 min (purity: 99.7%).

Workup

  1. stirringthe mixture is stirred at rt for 5 additional hours
  2. customsolvents are evaporated
  3. customThe resulting crude yellow product is purified by preparative HPLC

Sources & evidence

ORD record
ord-87d417c71820492eba5494b65bc4b101
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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