Pyridine → HCID 86305717, compound

HRID 712607Notes

Reaction equation

HRID 712607 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[N:16][C:15]3[NH:14][CH2:13][CH2:12][O:11][C:10]=3[CH:9]=2)[CH:5]=[N:6][CH:7]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[N:16][C:15]3[N:14]([C:24](=[O:26])[CH3:25])[CH2:13][CH2:12][O:11][C:10]=3[CH:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 117667226HCID 117667226, compound

Product 1

HCID 86305717HCID 86305717, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(5-fluoro-pyridin-3-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (350 mg, 1.5 mmol) (which is synthesized according to the procedure for Step 1 of Example 12) in DCM (100 mL) is added pyridine (1.7 g 18 mmol), then acetyl chloride (710 mg 9.1 mmol) is added dropwise. The solution is stirred at room temperature for 16 hrs and the solvent is removed. The residue is purified by preparative HPLC to give 54 mg of the titled product.

Workup

  1. customthe solvent is removed
  2. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-be4f406bc46c41e9b0b14a9d7eff7d94
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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