Dimethylformamide → HCID 89228777, compound

HRID 869901Notes

Reaction equation

HRID 869901 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]#[N:7])=[C:4]([Cl:11])[N:3]=1.CN(C=O)C.[H-].[Na+].[F:19][C:20]1([F:35])[O:24][C:23]2[CH:25]=[CH:26][C:27]([C:29]3([C:32](Cl)=[O:33])[CH2:31][CH2:30]3)=[CH:28][C:22]=2[O:21]1>O1CCCC1.O>[Cl:11][C:4]1[N:3]=[C:2]([NH:1][C:32]([C:29]2([C:27]3[CH:26]=[CH:25][C:23]4[O:24][C:20]([F:35])([F:19])[O:21][C:22]=4[CH:28]=3)[CH2:31][CH2:30]2)=[O:33])[CH:9]=[C:8]([CH3:10])[C:5]=1[C:6]#[N:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 137971676-Amino-2-chloro-4-methylpyridine-3-carbonitrileHCID 575168501-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl chloride

Product 1

HCID 89228777HCID 89228777, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Amino-2-chloro-4-methylnicotinonitrile (252 mg, 1.50 mmol) was dissolved in a mixture of anhydrous N,N′ dimtheylformamide (DMF, 0.5 mL) and anhydrous tetrahydrofuran (THF, 4.5 mL). The reaction tube was placed in a beaker full of room temperature water to help maintain the reaction temperature. Sodium hydride (84.23 mg, 2.106 mmol, 60% by weight in mineral oil) was added and the resulting suspension was allowed to stir for 5 minutes. 1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (392.0 mg, 1.5 mmol) was added and the reaction mixture turned dark red. The crude material was evaporated to dryness, re-dissolved in a minimum of dichloromethane, and purified on 12 g of silica utilizing a gradient of 0-50% ethyl acetate in hexanes to yield the pure product as a pale yellow solid (0.589 g, 63%). ESI-MS m/z calc. 391.0. found 392.0 (M+1)+. Retention time 2.06 minutes.

Workup

  1. customwas placed in a beaker full of room temperature
  2. temperatureto help maintain the reaction temperature
  3. customThe crude material was evaporated to dryness
  4. dissolutionre-dissolved in a minimum of dichloromethane
  5. custompurified on 12 g of silica utilizing a gradient of 0-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4cbc0db40bd84425a7277f54efd50c95
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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