Triethylamine → HCID 86702333, compound

HRID 2279079Notes

Reaction equation

HRID 2279079 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11]([Cl:18])[N:10]=1.[Cl:19][C:20]1[CH:21]=[C:22]([NH2:28])[C:23]([O:26][CH3:27])=[N:24][CH:25]=1>C(#N)C>[Cl:18][C:11]1[N:10]=[C:9]([NH:28][C:22]2[C:23]([O:26][CH3:27])=[N:24][CH:25]=[C:20]([Cl:19])[CH:21]=2)[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 451221815-Chloro-2-methoxypyridin-3-amine

Product 1

HCID 86702333HCID 86702333, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Triethylamine (2.7 mL) and a catalytic amount of 4-diaminopyrimidine were added to a solution of 2,6-dichloro-3-nitropyridine (639 mg, 3.31 mmol) and 5-chloro-2-methoxy pyridin-3-amine (Preparation 23, 501 mg, 3.16 mmol) in acetonitrile (20 mL) and the resulting mixture was stirred overnight at 90° C. Solvent was then removed under reduced pressure until a solid precipitated. The solid was filtered, washed with acetonitrile and dried. The solid was then treated with dichloromethane, filtered, washed with more dichloromethane and the combined filtrate and washings were concentrated to dryness under reduced pressure to yield the title compound (390 mg 30%) as an orange solid.

Workup

  1. customSolvent was then removed under reduced pressure until a solid
  2. customprecipitated
  3. filtrationThe solid was filtered
  4. washwashed with acetonitrile
  5. customdried
  6. additionThe solid was then treated with dichloromethane
  7. filtrationfiltered
  8. washwashed with more dichloromethane
  9. concentrationthe combined filtrate and washings were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f2e83d4dc01c42449d4561a80ba1b238
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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