HCID 117640744, compound → N-(5-chloro-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-1-(2,2-difluorobenzo [d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 869910Notes

Reaction equation

HRID 869910 reaction equation
[Cl:1][C:2]1[C:3]([C:25]2[CH:26]=[N:27][C:28]([O:31]C)=[CH:29][CH:30]=2)=[N:4][C:5]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:22])([F:21])[O:20][C:16]=4[CH:15]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:6][CH:7]=1>O1CCOCC1.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:22])([F:21])[O:20][C:16]=4[CH:15]=3)[CH2:12][CH2:13]2)=[O:10])=[N:4][C:3]=1[C:25]1[CH:30]=[CH:29][C:28](=[O:31])[NH:27][CH:26]=1

Participants

4

Reactant 1

HCID 117640744HCID 117640744, compound

Product 1

HCID 117640729N-(5-chloro-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-1-(2,2-difluorobenzo [d][1,3]dioxol-5-yl)cyclopropanecarboxamideYield 22.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

N-(3-Chloro-6′-methoxy-2,3′-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (124 mg, 0.270 mmol) was dissolved in a mixture of 1.2 mL of 1,4-dioxane and 0.6 mL of 4M aqueous hydrochloric acid. This solution was heated at 90° C. for 5 hours. The crude reaction mixture was quenched with triethylamine and then evaporated to dryness. The crude product was then partitioned between dichloromethane and water. The organic layer was separated, dried over sodium sulfate, and then purified on 4 g of silica gel utilizing a gradient of 0-5% methanol in dichloromethane to yield N-(5-chloro-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide as a white solid (27 mg, 22%). ESI-MS m/z calc. 445.1. found 445.9 (M+1)+. Retention time 1.62 minutes.

Workup

  1. customThe crude reaction mixture
  2. customwas quenched with triethylamine
  3. customevaporated to dryness
  4. customThe crude product was then partitioned between dichloromethane and water
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. custompurified on 4 g of silica gel utilizing a gradient of 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-28bd94c26d434269a656e989206b5da2
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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