2-Amino-5-chloropyridine → HCID 21906507, compound

HRID 988648Notes

Reaction equation

HRID 988648 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[C:8]([CH:13]=1)[C:9]([O:11]C)=O)([O-])=O.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=1.C[Mg]Br>C1COCC1>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[C:8]([CH:13]=1)[C:9]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=1)=[O:11]

Participants

5

Reactant 3

HCID 661742-Amino-5-chloropyridine2×HCID 21906430HCID 21906430, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21906507HCID 21906507, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 5-nitro-2-[1-(4-pyridinyl)piperidin-4-ylmethylamino]benzoate (400 mg, 1.08 mmol) was treated with the magnesium salt of 2-amino-5-chloropyridine [freshly prepared by the addition of methyl magnesium bromide (2.16 mmol) to a solution of 2-amino-5-chloropyridine (2.16 mmol) in THF (11 mL)] and the mixture was heated at reflux. After 3 h, the mixture was cooled, sonicated, and the resulting solid (645 mg) collected by filtration. Using a similar procedure to that described in Example 2-B, the crude material was reduced to yield 370 mg of the titled compound; which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe mixture was cooled
  4. customsonicated
  5. filtrationthe resulting solid (645 mg) collected by filtration

Sources & evidence

ORD record
ord-9b51fd5e9bac4fbb8dd758797a25e186
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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