Triethylamine → HCID 22283099, compound

HRID 1063027Notes

Reaction equation

HRID 1063027 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-2b577c823abe44dab76a69d49a549e36
Source dataset
uspto-grants-2005_11
Patent number
US06963000B2

Reaction notes

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