Water → HCID 10498284, compound

HRID 2229307Notes

Reaction equation

HRID 2229307 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1.[Br:16][C:17]1[CH:18]=[C:19]([C:24]([NH:26][C:27]2[C:28]([NH:34][CH2:35][CH3:36])=[N:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:25])[C:20](Cl)=[N:21][CH:22]=1.O>N1C=CC=CC=1>[Br:16][C:17]1[CH:22]=[N:21][C:20]2[N:34]([CH2:35][CH3:36])[C:28]3[N:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=3[NH:26][C:24](=[O:25])[C:19]=2[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18466625HCID 18466625, compound

Product 1

HCID 10498284HCID 10498284, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A 1 M solution of NaHMDS in THF (167.5 mL, 167.5 mmol) was slowly added to a solution of 5-bromo-2-chloro-N-{2-(ethylamino)-6-choro-3-pyridinyl}-3-pyridinecarboxamide (28.4 g, 72.8 mmol) in pyridine (146 mL) heated to 50° C. The reaction mixture was stirred at 50° C. for 1.5 h. The mixture was then poured into a mixture of water and ice (1 L) and, after 1 h, the resulting suspension was filtered. The solid was washed with water and dried under reduced pressure to give the title compound (23.4 g, 91% yield).

Workup

  1. filtrationthe resulting suspension was filtered
  2. washThe solid was washed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-fb3757a1252646038f539f8f8acc6731
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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