3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 56961393, compound

HRID 1958155Notes

Reaction equation

HRID 1958155 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([NH2:14])[CH:11]=[N:10][C:9]=2[O:15][C@@H:16]([CH3:21])[C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1.Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([NH:14][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=3)[CH:11]=[N:10][C:9]=2[O:15][C@@H:16]([CH3:21])[C:17]([F:18])([F:20])[F:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 67281095HCID 67281095, compound

Product 1

HCID 56961393HCID 56961393, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

6-(4-Chloro-phenyl)-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyrazin-2-ylamine (0.100 g, 315 μmol) was dissolved in dried pyridine (1.0 mL), nicotinoyl chloride hydrochloride (61.6 mg, 346 μmol) was added and the suspension was stirred at 140° C. for 10 minutes in the microwave. The solvent was evaporated and the crude material was purified by flash chromatography (silica gel, 10 g, 0% to 50% CH2Cl2/MeOH/NH3 9/1/0.1) to give 0.121 g (91%) of the title compound as white solid; LC-MS (UV peak area/ESI) 100%, 423.0821 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was purified by flash chromatography (silica gel, 10 g, 0% to 50% CH2Cl2/MeOH/NH3 9/1/0.1)

Sources & evidence

ORD record
ord-30251070516e4cc2be6aed82d24e4f80
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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