Acetyl chloride → HCID 73053653, compound

HRID 870442Notes

Reaction equation

HRID 870442 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([C:19]3[C:20](=[O:32])[N:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:22]([CH3:25])[C:23]=3[CH3:24])=[O:18])=[N:14][CH:15]=2)[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[C:40](Cl)(=[O:42])[CH3:41].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.C1COCC1>[C:40]([NH:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([C:19]3[C:20](=[O:32])[N:21]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:22]([CH3:25])[C:23]=3[CH3:24])=[O:18])=[N:14][CH:15]=2)[CH:5]=[CH:4][N:3]=1)(=[O:42])[CH3:41]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 73053628HCID 73053628, compound

Product 1

HCID 73053653HCID 73053653, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-((2-amino-3-chloropyridin-4-yl)oxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (60 mg, 0.13 mmol), and Et3N (26.3 mg, 0.26 mmol) in CH2Cl2 (1 mL) and THF (2 mL) was added acetyl chloride (20 mg, 0.26 mmol). The reaction was stirred at rt for 3 hours, then treated with saturated Na2CO3 aqueous solution (2 mL). The resulted mixture was continued to stir at rt for 5 minutes, then concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=50/1) to give the title compound as a light beige solid (15 mg, 22.7%).

Workup

  1. stirringto stir at rt for 5 minutes
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=50/1)

Sources & evidence

ORD record
ord-c5ad6a0c070e42e1972a91ad19d15754
Source dataset
uspto-grants-2015_03
Patent number
US08969388B1

Reaction notes

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