3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 22282252, compound

HRID 1062630Notes

Reaction equation

HRID 1062630 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH2:22])[S:14][C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].Cl.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH3:4][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH:22][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=3)[S:14][C:15]=2[C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 11335869HCID 11335869, compound

Product 1

HCID 22282252HCID 22282252, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of [4-[4-(1,1-dimethylethyl)phenyl]-5-(4-pyridyl)-1,3-thiazol-2-yl]amine (0.50 g, 1.62 mmol) and 4-dimethylaminopyridine (0.06 g, 0.49 mmol) in N,N-dimethylacetamide (5 mL) was added nicotinoyl chloride hydrochloride (0.43 g, 2.42 mmol) and the mixture was stirred at 70° C. for 14 h. To the reaction mixture was poured aqueous sodium hydrogencarbonate solution and the precipitated solid was collected by filtration. The obtained solid was washed with water and dried. The crude crystals were recrystallized from ethanol to give the title compound (0.49 g, yield 73%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe obtained solid was washed with water
  3. customdried
  4. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-bbd5e67fd7384ecea1f448cb1defe3a9
Source dataset
uspto-grants-2005_11
Patent number
US06962933B1

Reaction notes

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