Sodium hydride → 6-Chloro-2-methyl-4-({5-[(morpholin-4-yl)carbonyl]pyridin-2-yl}amino)-2,3-dihydropyridazin-3-one

HRID 1916073Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[C:20](=[O:27])[N:21]([CH3:26])[N:22]=[C:23]([Cl:25])[CH:24]=1>CN(C)C=O>[Cl:25][C:23]1[CH:24]=[C:19]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[O:9])=[CH:6][N:7]=2)[C:20](=[O:27])[N:21]([CH3:26])[N:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(6-Amino-pyridin-3-yl)-morpholin-4-yl-methanone (2.921 g, 14.11 mmol) was suspended in 50 mL dimethylformamide and cooled to 0° C. Sodium hydride 60% suspension in mineral oil (847 mg, 21.2 mmol) was added. This was stirred at room temperature for 30 minutes and was cooled to 0° C. 4,6-Dichloro-2-methyl-2H-pyridazin-3-one (1.256 g, 7.056 mmol) was added. After 2 hours, this was partitioned between saturated aqueous ammonium chloride solution and ethylacetate. The ethylacetate layer was dried over anhydrous MgSO4, concentrated in vacuo, and purified by flash chromatography (2% MeOH/CH2Cl2) to yield 6-Chloro-2-methyl-4-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-2H-pyridazin-3-one (732 mg, 2.09 mmol). MS (ESI) 350.1 (M+H)+.

Workup

temperaturewas cooled to 0° C
waitAfter 2 hours
customthis was partitioned between saturated aqueous ammonium chloride solution and ethylacetate
dry with materialThe ethylacetate layer was dried over anhydrous MgSO4
concentrationconcentrated in vacuo
custompurified by flash chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-27fb7be8e32c4b72ae4df3649de3fab5
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618098B2

Reaction notes

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