Triethylamine → HCID 22283099, compound

HRID 2308504Notes

Reaction equation

HRID 2308504 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][CH:4]=1.C([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])C.[C:25](Cl)(=[O:32])[C:26]1C=CN=C[CH:27]=1.C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.O1CCOCC1.O>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:25](=[O:32])[C:26]3[CH:22]=[CH:21][N:20]=[C:23]([CH3:24])[CH:27]=3)[S:11][C:7]=2[C:6]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 417436Pyridine-4-carbonyl chlorideHCID 516892Sodium BicarbonateHCID 22283380HCID 22283380, compound

Product 1

HCID 22283099HCID 22283099, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

0.21 g of 4-methoxy-7-thiophen-2-yl-benzothiazol-2-yl-amine (0.0008 Mol) together with 0.27 ml triethylamine (0.002 Mol), 0.01 g of DMAP and 0.20 g isonicotinic acid chloride (0.001 Mol) were heated to reflux for 20 hrs. in dioxane (10 ml). After cooling to room temperature water (20 ml) and sat. NaHCO3 (15 ml) were added. A precipitation formed, which was filtered, washed with water and dried. This crude product was subjected to column chromatography (silicagel, ethyl acetate) to yield the title compound as a yellow solid (58%); F.p.: 203-211° C. (dec.).

Workup

  1. temperatureto reflux for 20 hrs
  2. additionwere added
  3. customA precipitation
  4. customformed
  5. filtrationwhich was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-0a0719fa909f46239d50544320278d3f
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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