Acetyl chloride → HCID 117667744, compound

HRID 712653Notes

Reaction equation

HRID 712653 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16](=[N:17][CH:18]=2)[NH:15][CH2:14][CH2:13][CH2:12]3)[CH:6]=[N:7][CH:8]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16](=[N:17][CH:18]=2)[N:15]([C:28](=[O:30])[CH3:29])[CH2:14][CH2:13][CH2:12]3)[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 117667784HCID 117667784, compound

Product 1

HCID 117667744HCID 117667744, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(5-Trifluoromethyl-pyridin-3-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine (200 mg, 0.72 mmol), whose synthesis is described in Step 1 of Example 4, is dissolved in DCM (25 mL). Triethylamine (220 mg, 2.1 mmol) is added followed by the addition of acetyl chloride (67 mg, 0.86 mmol) under N2 atmosphere at 0° C. The mixture is stirred at room temperature for 3 hrs. The solvent is removed and the residue is purified by preparative TLC to give 43 mg of the titled product.

Workup

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

Sources & evidence

ORD record
ord-96747da4e87b4952a9db2319752ef557
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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