Triethylamine → HCID 89228784, compound

HRID 869900Notes

Reaction equation

HRID 869900 reaction equation
[F:1][C:2]1([F:17])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14](Cl)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.[Cl:18][C:19]1[N:24]=[C:23]([NH2:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[CH3:27].CCN(CC)CC>ClCCl>[Cl:18][C:19]1[N:24]=[C:23]([NH:25][C:14]([C:11]2([C:9]3[CH:8]=[CH:7][C:5]4[O:6][C:2]([F:17])([F:1])[O:3][C:4]=4[CH:10]=3)[CH2:13][CH2:12]2)=[O:15])[CH:22]=[C:21]([CH3:26])[C:20]=1[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 575168501-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl chlorideHCID 735538296-Chloro-4,5-dimethylpyridin-2-amine

Product 1

HCID 89228784HCID 89228784, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (676 mg, 2.6 mmol) and 6-chloro-4,5-dimethylpyridin-2-amine (314 mg, 2.0 mmol), dichloromethane (7.0 mL) and Et3N (835 μL, 6 mmol) were added. The reaction was stirred at room temperature for 1 hour. The reaction was diluted with dichloromethane and washed with 1N HCl (3×) and saturated aqueous NaHCO3 (3×). The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to yield N-(6-chloro-4,5-dimethylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (560 mg, 73%). ESI-MS m/z calc. 380.07. found 381.3 (M+1)+. Retention time 2.18 minutes.

Workup

  1. washwashed with 1N HCl (3×) and saturated aqueous NaHCO3 (3×)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f60411c0df664517ac7fed7c5bfc7d11
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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