Triethylamine → HCID 86584939, compound

HRID 2250739Notes

Reaction equation

HRID 2250739 reaction equation
N[C:2]1[S:3][CH:4]=[C:5]([C:7]2[C:15]3[S:14][C:13]([NH2:16])=[N:12][C:11]=3[C:10]([O:17][CH3:18])=[CH:9][CH:8]=2)[N:6]=1.[H-].[Na+].[CH2:21](N(CC)CC)C.[N:28]1([C:34](Cl)=[O:35])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>O1CCOCC1.O>[CH3:18][O:17][C:10]1[C:11]2[N:12]=[C:13]([NH:16][C:34]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:35])[S:14][C:15]=2[C:7]([C:5]2[N:6]=[C:2]([CH3:21])[S:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 848104-Morpholinecarbonyl chlorideHCID 22283133HCID 22283133, compound

Product 1

HCID 86584939HCID 86584939, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

0.07 g of 7-(2-Amino-thiazol-4-yl)-4-methoxy-benzothiazol-2-yl-amine (0.00025 Mol) were suspended in dioxane (4 ml) and treated with 0.028 g of NaH (60% dispersion in oil) (0.0006 Mol) for 1 h at room temperature. Then 0.11 ml of triethylamine (0.00076 Mol) and 0.07 ml of morpholine-4-carbonylchloride (0.0006 Mol) were added and the reaction mixture was stirred at room temperature for 3 hrs. Then water (15 ml) was added and the reaction mixture was extracted with ethyl acetate (4×, 20 ml each). The combined organic phases were dried over Na2SO4, filtered and evaporated. The residue was subjected to column chromatography (silicagel, ethyl acetate). The title compound was obtained as a light yellow solid (61%); F.p.: 223-226° C. (dec.).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (4×, 20 ml each)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-1f594d57cebb47d799d068d76a9f6f34
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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